3-Bromo-5-meth­oxy-4-(4-methyl­piperidin-1-yl)furan-2(5H)-one

Xin-Ping Wei; Jian-Hua Fu; Yue-He Tan; Zhao-Yang Wang

doi:10.1107/S1600536811008804

. 2011 Mar 12;67(Pt 4):o862. doi: 10.1107/S1600536811008804

3-Bromo-5-methoxy-4-(4-methylpiperidin-1-yl)furan-2(5H)-one

Xin-Ping Wei ^a, Jian-Hua Fu ^a, Yue-He Tan ^a, Zhao-Yang Wang ^a,^*

PMCID: PMC3099783 PMID: 21754143

Abstract

There are two molecules in the asymmetric unit of title compound, C₁₁H₁₆BrNO₃, which was obtained via the tandem Michael addition–elimination reaction of 3,4-dibromo-5-methoxyfuran-2(5H)-one and 4-methylpiperidine in the presence of potassium fluoride. The furanone rings are approximately planar [maximum atomic deviations of 0.026 (2) and 0.015 (2) Å, respectively]. The packing is stabilized by weak intermolecular C—H⋯O and C—H⋯Br interactions.

Related literature

For biologically active 4-amino-2(5H)-furanones, see: Lattmann et al. (1999 ▶, 2005 ▶, 2006 ▶). For natural and synthetic products of 2(5H)-furanones, see: Zhou et al. (2009 ▶). For the synthesis of the title compound, see: Song, Wang et al. (2009 ▶). For a related structure, see Song, Li et al. (2009 ▶). graphic file with name e-67-0o862-scheme1.jpg

Experimental

Crystal data

C₁₁H₁₆BrNO₃
M _r = 290.15
Monoclinic,
a = 12.681 (3) Å
b = 10.481 (2) Å
c = 19.947 (4) Å
β = 103.312 (3)°
V = 2579.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 3.18 mm⁻¹
T = 298 K
0.32 × 0.22 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.436, T _max = 0.529
9692 measured reflections
4532 independent reflections
1918 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.109
S = 1.08
4532 reflections
294 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008804/ez2228sup1.cif

e-67-0o862-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008804/ez2228Isup2.hkl

e-67-0o862-Isup2.hkl^{(222KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2	0.98	2.56	3.486 (7)	157
C2—H2⋯O6ⁱ	0.98	2.58	3.505 (7)	158
C2—H2⋯Br1ⁱⁱ	0.98	3.06	3.718 (6)	126

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Symmetry codes: (i) Inline graphic ; (ii) .

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)-Furanone structures are found in many natural and synthetic products (Zhou et al., 2009). At the same time, 4-amino-2(5H)-furanones have shown antibacterial activity and antibiotic activity against MRSA (Lattmann et al., 1999; Lattmann et al., 2006; Lattmann et al., 2005).

Attracted by versatile 4-amino-2(5H)-furanones, we synthesized the title compound with 3,4-dibromo-5-methoxyfuran-2(5H)-one and 4-methylpiperidine in the presence of potassium fluoride via the tandem Michael addition-elimination reaction. Due to the presence of the 2(5H)-furanone moiety and polyfunctional groups (carboxyl, amino, halo) the title compound is expected to be a biologically active product and excellent ligand.

In the title compound, (I), two crystallographically independent molecules with R and S spatial configurations are present in the asymmetric unit. The furanone ring is approximately planar, similar to that found in a related compound (Song, Li et al. 2009). Additionally, the molecules are linked by weak C—H···O and C—H···Br intermolecular interactions.

Experimental

The precursor 3,4-dibromo-5-methoxyfuran-2(5H)-furanone was prepared according to the literature procedure (Song, Wang et al., 2009). After the mixture of 3,4-dibromo-5-methoxyfuran-2(5H)-furanone (2.0 mmol) and potassium fluoride (6.0 mmol) was dissolved in absolute tetrahydrofuran (2.0 mL) under nitrogen atmosphere, a tetrahydrofuran solution of 4-methylpiperidine (2.0 mmol) was added. The reaction was carried out under stirring at room temperature for 48 h. Once the reaction was complete, the solvents were removed under reduced pressure. The residual solid was dissolved in dichloromethane and extracted. The combined organic layers from the extraction were concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography with a gradient mixture of petroleum ether and ethyl acetate to give the product yielding (I) 0.2988 g (51.7%).