(5S)-3-Chloro-5-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yloxy]-4-(4-methyl­piperidin-1-yl)furan-2(5H)-one

doi:10.1107/S1600536811005216

Acta Crystallogr Sect E Struct Rep Online. 2011 March 1; 67(Pt 3): o656.

Published online 2011 February 19. doi: 10.1107/S1600536811005216

PMCID: PMC3051989

(5S)-3-Chloro-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-4-(4-methylpiperidin-1-yl)furan-2(5H)-one

Xiao-Mei Wang,^a Jian-Hua Fu,^a Song-Liang Cai,^a and Zhao-Yang Wang^a^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People’s Republic of China

Correspondence e-mail: wangwangzhaoyang/at/tom.com

Received January 25, 2011; Accepted February 11, 2011.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

The title compound, C₂₀H₃₂ClNO₃, was obtained via a tandem asymmetric Michael addition–elimination reaction of (5S)-3,4-dichloro-5-(l-menthyloxy)furan-2(5H)-one and 4-methylpiperidine in the presence of potassium fluoride. The furanone ring is approximately planar [maximum atomic deviation = 0.022 (2) Å] while the cyclohexane ring adopts a chair conformation. Weak intermolecular C—H (...)

O hydrogen bonding is present in the crystal structure.

Related literature

The title compound is a derivative of 4-amino-2(5H)-furanone. For the biological activity of 4-amino-2(5H)-furanones, see: Lattmann et al. (2005

); Prasad & Gandi (2010

); Steenackers et al. (2010

). For asymmetric Michael addition reactions of 2(5H)-furanone and for the synthesis of the title compound, see: Song et al. (2009

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Object name is e-67-0o656-scheme1.jpg Object name is e-67-0o656-scheme1.jpg

Experimental

Crystal data

C₂₀H₃₂ClNO₃
M _r = 369.92
Orthorhombic,
a = 9.187 (5) Å
b = 9.248 (5) Å
c = 24.987 (12) Å
V = 2122.9 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.28 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T _min = 0.940, T _max = 0.947
12264 measured reflections
4505 independent reflections
2620 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.112
S = 1.01
4505 reflections
231 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1921 Friedel pairs
Flack parameter: 0.10 (8)

Data collection: APEX2 (Bruker, 2008

); cell refinement: SAINT (Bruker, 2008

); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008

); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008

); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997

); software used to prepare material for publication: SHELXL97.

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005216/go2003sup1.cif

Click here to view.^{(21K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005216/go2003Isup2.hkl

Click here to view.^{(221K, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

supplementary crystallographic information

Comment

2(5H)-furanones are heterocyclic carbonyl compounds, which are widespread in natural and in synthetic products (Prasad & Gandi, 2010; Steenackers et al., 2010). 5-menthyloxy-3,4-dihalo-2(5H)-furanones, being a kind of chiral synthons, are widely used in asymmetric Michael addition-elimination tandem reactions (Song et al., 2009). 4-amino-2(5H)-furanones show an antibiotic activity against Staphylococcus aureus (Lattmann et al., 2005).

We are interested in the tandem Michael addition-elimination reaction of the chiral synthon 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone and 4-methylpiperidine in the presence of potassium fluoride. The structure of the title compound (I) is illustrated in Fig. 1. The crystal structure of the title compound, which has four chiral centers (C4(S), C5(R), C6(S), C9(R)) contains a five-membered furanone ring and a six-membered cyclohexane ring connected each other via C4—O3—C5 ether bond. The furanone ring of C4—O1—C1—C2—C3 is approximately planar, whereas a six-membered cyclohexane ring displays a chair conformation. At the same time, the furanone ring is connected to piperidine heterocycle via C3—N1 bond.

Experimental

The precursor 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone was prepared according to the literature procedure (Song et al., 2009). After the mixture of 3,4-dichloro-5-(S)-(l-menthyloxy)-2(5H)-furanone (2.0 mmol) and potassium fluoride (6.0 mmol) was dissolved in absolute tetrahydrofuran (2.0 mL) under nitrogen atmosphere, tetrahydrofuran solution of 4-methylpiperidine (2.0 mmol) was added. The reaction was carried out by stirring at room temperature for 24 h. Once the reaction was complete, the solvents were removed under reduced pressure. The residual solid was dissolved in dichloromethane. Then the combined organic layers from extraction were concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography with the gradient mixture of petroleum ether and ethyl acetate to give the product yielding (I) 0.5685 g (76.8%).

Figures

Fig. 1.

The molecular structure of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.

Fig. 2.

Perspective view of the crystal packing.

Crystal data

C₂₀H₃₂ClNO₃	F(000) = 800
M_r = 369.92	D_x = 1.157 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2408 reflections
a = 9.187 (5) Å	θ = 2.7–19.8°
b = 9.248 (5) Å	µ = 0.20 mm⁻¹
c = 24.987 (12) Å	T = 298 K
V = 2122.9 (19) Å³	Block, colourless
Z = 4	0.32 × 0.30 × 0.28 mm

Data collection

Bruker APEXII area-detector diffractometer	4505 independent reflections
Radiation source: fine-focus sealed tube	2620 reflections with I > 2σ(I)
graphite	R_int = 0.038
and ω scans	θ_max = 26.8°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.940, T_max = 0.947	k = −11→10
12264 measured reflections	l = −31→31

Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0492P)² + 0.001P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4505 reflections	Δρ_max = 0.13 e Å⁻³
231 parameters	Δρ_min = −0.16 e Å⁻³
24 restraints	Absolute structure: Flack (1983), 1921 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (8)

Special details

Experimental. Data for (I): [α]^20°_D = 96.2° (c 0.600, CH₃CH₂OH); ¹H NMR (400 MHz, CDCl₃, TMS): 0.769 (3H, d, J = 6.8 Hz, CH₃), 0.831-0.934 (7H, m, CH, 2CH₃), 0.981-1.166 (5H, m, CH₂, CH₃), 1.212-1.756 (9H, m, 3CH, 3CH₂), 2.160-2.271 (2H, m, CH₂), 2.974-3.090 (2H, m, CH₂), 3.529-3.581 (1H, m, CH), 4.079-4.335 (2H, m, CH₂), 5.762 (1H, s, CH), ESI-MS, m/z (%): Calcd for C₂₀H₃₂ClNO₃⁺([M+H]⁺): 370.21(100.0), 372.20(32.0), Found: 370.29 (45.0), 372.33(15.0).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
Cl1	0.60861 (9)	−0.13528 (9)	0.17373 (3)	0.0923 (3)
C3	0.7320 (3)	0.0841 (3)	0.23600 (8)	0.0557 (6)
C4	0.8425 (3)	0.0853 (3)	0.28119 (8)	0.0578 (6)
H4	0.9252	0.1479	0.2725	0.069*
C2	0.7123 (3)	−0.0578 (3)	0.22267 (9)	0.0621 (7)
C1	0.8084 (3)	−0.1478 (4)	0.25291 (10)	0.0681 (7)
C5	0.8604 (3)	0.1414 (3)	0.37500 (8)	0.0621 (6)
H5	0.9630	0.1522	0.3650	0.074*
C6	0.8125 (3)	0.2733 (3)	0.40633 (9)	0.0702 (8)
H6	0.7085	0.2604	0.4136	0.084*
C7	0.8883 (4)	0.2751 (4)	0.46068 (10)	0.0956 (9)
H7A	0.9919	0.2897	0.4554	0.115*
H7B	0.8517	0.3558	0.4815	0.115*
C10	0.8414 (4)	0.0021 (4)	0.40651 (11)	0.0960 (11)
H10A	0.8791	−0.0780	0.3856	0.115*
H10B	0.7385	−0.0149	0.4124	0.115*
C11	0.8269 (4)	0.4160 (4)	0.37596 (11)	0.0878 (10)
H11	0.7799	0.4016	0.3412	0.105*
C9	0.9194 (5)	0.0065 (4)	0.46042 (11)	0.1115 (13)
H9	1.0238	0.0194	0.4538	0.134*
C8	0.8648 (6)	0.1363 (5)	0.49177 (11)	0.1279 (14)
H8A	0.7619	0.1245	0.4993	0.153*
H8B	0.9160	0.1419	0.5257	0.153*
C13	0.7463 (5)	0.5387 (4)	0.40314 (16)	0.1393 (16)
H13A	0.7508	0.6236	0.3811	0.209*
H13B	0.7906	0.5586	0.4371	0.209*
H13C	0.6465	0.5117	0.4084	0.209*
C14	0.9795 (6)	0.4590 (5)	0.36473 (16)	0.1399 (16)
H14A	1.0262	0.4871	0.3975	0.210*
H14B	0.9802	0.5388	0.3402	0.210*
H14C	1.0308	0.3788	0.3493	0.210*
C18	0.7583 (3)	0.4266 (3)	0.17613 (10)	0.0709 (7)
H18A	0.8318	0.3755	0.1557	0.085*
H18B	0.7946	0.5232	0.1833	0.085*
C19	0.7345 (3)	0.3499 (3)	0.22804 (9)	0.0711 (7)
H19A	0.8266	0.3401	0.2467	0.085*
H19B	0.6696	0.4065	0.2504	0.085*
C16	0.5572 (3)	0.2862 (3)	0.13592 (10)	0.0750 (8)
H16A	0.4646	0.2930	0.1174	0.090*
H16B	0.6226	0.2290	0.1140	0.090*
C15	0.5354 (3)	0.2122 (3)	0.18891 (9)	0.0691 (7)
H15A	0.4628	0.2643	0.2095	0.083*
H15B	0.4996	0.1149	0.1830	0.083*
C17	0.6204 (3)	0.4374 (3)	0.14313 (10)	0.0755 (8)
H17	0.5498	0.4957	0.1631	0.091*
C20	0.6467 (4)	0.5099 (4)	0.08935 (13)	0.1153 (13)
H20A	0.5553	0.5251	0.0716	0.173*
H20B	0.7073	0.4490	0.0676	0.173*
H20C	0.6941	0.6012	0.0948	0.173*
N1	0.6712 (2)	0.2061 (3)	0.21914 (8)	0.0635 (6)
O3	0.77190 (15)	0.13329 (19)	0.32666 (5)	0.0606 (4)
O1	0.88796 (18)	−0.0624 (2)	0.28665 (6)	0.0692 (5)
O2	0.8292 (2)	−0.2765 (3)	0.25154 (9)	0.0958 (7)
C12	0.8980 (9)	−0.1363 (5)	0.49012 (16)	0.193 (2)
H12A	0.7961	−0.1514	0.4966	0.290*
H12B	0.9489	−0.1329	0.5237	0.290*
H12C	0.9355	−0.2142	0.4688	0.290*

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0966 (5)	0.0925 (6)	0.0878 (5)	−0.0040 (5)	−0.0238 (4)	−0.0303 (4)
C3	0.0532 (14)	0.0716 (19)	0.0423 (11)	−0.0039 (13)	0.0037 (10)	−0.0047 (12)
C4	0.0566 (14)	0.0663 (19)	0.0507 (13)	−0.0053 (12)	−0.0014 (11)	−0.0038 (12)
C2	0.0612 (16)	0.072 (2)	0.0534 (13)	−0.0043 (14)	−0.0029 (12)	−0.0094 (13)
C1	0.0596 (15)	0.077 (2)	0.0677 (16)	0.0055 (16)	0.0053 (13)	−0.0158 (17)
C5	0.0649 (16)	0.0735 (17)	0.0478 (12)	−0.0011 (14)	−0.0084 (11)	−0.0026 (13)
C6	0.0673 (16)	0.092 (2)	0.0511 (13)	0.0086 (15)	−0.0004 (12)	−0.0171 (15)
C7	0.132 (3)	0.100 (2)	0.0542 (15)	−0.003 (2)	−0.0164 (17)	−0.0124 (17)
C10	0.132 (3)	0.092 (2)	0.0633 (16)	−0.020 (2)	−0.0195 (18)	0.0117 (17)
C11	0.126 (3)	0.078 (2)	0.0596 (16)	0.022 (2)	−0.0152 (17)	−0.0160 (16)
C9	0.173 (3)	0.094 (3)	0.0678 (18)	−0.024 (3)	−0.037 (2)	0.0227 (19)
C8	0.183 (4)	0.150 (3)	0.0514 (16)	−0.022 (3)	−0.016 (2)	0.002 (2)
C13	0.161 (4)	0.120 (3)	0.137 (3)	0.055 (3)	−0.042 (3)	−0.052 (3)
C14	0.165 (4)	0.103 (3)	0.152 (3)	0.002 (3)	0.053 (3)	0.013 (3)
C18	0.0791 (18)	0.0660 (18)	0.0678 (15)	−0.0153 (14)	−0.0104 (14)	0.0016 (14)
C19	0.0835 (19)	0.0686 (19)	0.0610 (15)	−0.0105 (16)	−0.0154 (14)	−0.0090 (14)
C16	0.0752 (18)	0.084 (2)	0.0663 (16)	−0.0017 (16)	−0.0243 (13)	−0.0002 (16)
C15	0.0592 (15)	0.0720 (18)	0.0760 (17)	−0.0043 (13)	−0.0121 (13)	−0.0002 (15)
C17	0.087 (2)	0.0695 (19)	0.0700 (15)	−0.0068 (17)	−0.0108 (15)	0.0073 (15)
C20	0.144 (3)	0.112 (3)	0.091 (2)	−0.029 (2)	−0.022 (2)	0.040 (2)
N1	0.0670 (13)	0.0634 (14)	0.0601 (11)	−0.0079 (12)	−0.0147 (10)	0.0039 (11)
O3	0.0557 (9)	0.0823 (12)	0.0436 (8)	0.0034 (9)	−0.0045 (7)	−0.0074 (9)
O1	0.0577 (10)	0.0779 (13)	0.0719 (10)	0.0108 (10)	−0.0093 (9)	−0.0086 (10)
O2	0.0908 (14)	0.0731 (15)	0.1237 (17)	0.0195 (12)	−0.0096 (12)	−0.0176 (14)
C12	0.339 (7)	0.136 (4)	0.105 (3)	−0.040 (5)	−0.072 (4)	0.049 (3)

Geometric parameters (Å, °)

Cl1—C2	1.708 (2)	C8—H8B	0.9700
C3—N1	1.327 (3)	C13—H13A	0.9600
C3—C2	1.366 (4)	C13—H13B	0.9600
C3—C4	1.519 (3)	C13—H13C	0.9600
C4—O3	1.381 (3)	C14—H14A	0.9600
C4—O1	1.435 (3)	C14—H14B	0.9600
C4—H4	0.9800	C14—H14C	0.9600
C2—C1	1.429 (4)	C18—C19	1.495 (4)
C1—O2	1.206 (4)	C18—C17	1.514 (4)
C1—O1	1.367 (3)	C18—H18A	0.9700
C5—O3	1.458 (3)	C18—H18B	0.9700
C5—C6	1.514 (4)	C19—N1	1.468 (3)
C5—C10	1.520 (4)	C19—H19A	0.9700
C5—H5	0.9800	C19—H19B	0.9700
C6—C7	1.526 (4)	C16—C15	1.504 (3)
C6—C11	1.529 (4)	C16—C17	1.525 (4)
C6—H6	0.9800	C16—H16A	0.9700
C7—C8	1.516 (4)	C16—H16B	0.9700
C7—H7A	0.9700	C15—N1	1.460 (3)
C7—H7B	0.9700	C15—H15A	0.9700
C10—C9	1.526 (4)	C15—H15B	0.9700
C10—H10A	0.9700	C17—C20	1.521 (4)
C10—H10B	0.9700	C17—H17	0.9800
C11—C14	1.484 (5)	C20—H20A	0.9600
C11—C13	1.516 (5)	C20—H20B	0.9600
C11—H11	0.9800	C20—H20C	0.9600
C9—C8	1.519 (5)	C12—H12A	0.9600
C9—C12	1.527 (5)	C12—H12B	0.9600
C9—H9	0.9800	C12—H12C	0.9600
C8—H8A	0.9700

N1—C3—C2	133.1 (2)	C11—C13—H13B	109.5
N1—C3—C4	120.7 (2)	H13A—C13—H13B	109.5
C2—C3—C4	106.1 (2)	C11—C13—H13C	109.5
O3—C4—O1	111.37 (19)	H13A—C13—H13C	109.5
O3—C4—C3	107.47 (18)	H13B—C13—H13C	109.5
O1—C4—C3	105.0 (2)	C11—C14—H14A	109.5
O3—C4—H4	110.9	C11—C14—H14B	109.5
O1—C4—H4	110.9	H14A—C14—H14B	109.5
C3—C4—H4	110.9	C11—C14—H14C	109.5
C3—C2—C1	110.4 (2)	H14A—C14—H14C	109.5
C3—C2—Cl1	130.7 (2)	H14B—C14—H14C	109.5
C1—C2—Cl1	118.6 (2)	C19—C18—C17	112.4 (2)
O2—C1—O1	120.2 (3)	C19—C18—H18A	109.1
O2—C1—C2	131.1 (3)	C17—C18—H18A	109.1
O1—C1—C2	108.7 (3)	C19—C18—H18B	109.1
O3—C5—C6	107.9 (2)	C17—C18—H18B	109.1
O3—C5—C10	108.7 (2)	H18A—C18—H18B	107.9
C6—C5—C10	112.4 (2)	N1—C19—C18	110.9 (2)
O3—C5—H5	109.2	N1—C19—H19A	109.5
C6—C5—H5	109.2	C18—C19—H19A	109.5
C10—C5—H5	109.2	N1—C19—H19B	109.5
C5—C6—C7	109.6 (2)	C18—C19—H19B	109.5
C5—C6—C11	114.4 (2)	H19A—C19—H19B	108.0
C7—C6—C11	113.1 (2)	C15—C16—C17	111.3 (2)
C5—C6—H6	106.3	C15—C16—H16A	109.4
C7—C6—H6	106.3	C17—C16—H16A	109.4
C11—C6—H6	106.3	C15—C16—H16B	109.4
C8—C7—C6	112.4 (3)	C17—C16—H16B	109.4
C8—C7—H7A	109.1	H16A—C16—H16B	108.0
C6—C7—H7A	109.1	N1—C15—C16	111.1 (2)
C8—C7—H7B	109.1	N1—C15—H15A	109.4
C6—C7—H7B	109.1	C16—C15—H15A	109.4
H7A—C7—H7B	107.8	N1—C15—H15B	109.4
C5—C10—C9	112.4 (3)	C16—C15—H15B	109.4
C5—C10—H10A	109.1	H15A—C15—H15B	108.0
C9—C10—H10A	109.1	C18—C17—C20	112.2 (3)
C5—C10—H10B	109.1	C18—C17—C16	108.8 (2)
C9—C10—H10B	109.1	C20—C17—C16	111.1 (2)
H10A—C10—H10B	107.9	C18—C17—H17	108.2
C14—C11—C13	110.2 (4)	C20—C17—H17	108.2
C14—C11—C6	114.0 (3)	C16—C17—H17	108.2
C13—C11—C6	112.4 (3)	C17—C20—H20A	109.5
C14—C11—H11	106.5	C17—C20—H20B	109.5
C13—C11—H11	106.5	H20A—C20—H20B	109.5
C6—C11—H11	106.5	C17—C20—H20C	109.5
C8—C9—C10	108.7 (3)	H20A—C20—H20C	109.5
C8—C9—C12	112.9 (4)	H20B—C20—H20C	109.5
C10—C9—C12	110.2 (3)	C3—N1—C15	123.8 (2)
C8—C9—H9	108.3	C3—N1—C19	123.74 (19)
C10—C9—H9	108.3	C15—N1—C19	112.4 (2)
C12—C9—H9	108.3	C4—O3—C5	115.85 (16)
C7—C8—C9	111.0 (3)	C1—O1—C4	109.6 (2)
C7—C8—H8A	109.4	C9—C12—H12A	109.5
C9—C8—H8A	109.4	C9—C12—H12B	109.5
C7—C8—H8B	109.4	H12A—C12—H12B	109.5
C9—C8—H8B	109.4	C9—C12—H12C	109.5
H8A—C8—H8B	108.0	H12A—C12—H12C	109.5
C11—C13—H13A	109.5	H12B—C12—H12C	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.98	2.44	3.376 (3)	160
C18—H18B···O2ⁱⁱ	0.97	2.54	3.393 (4)	147

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2003).

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