(S)-2-(1H-Imidazol-1-yl)-3-phenyl­propanol

Zuxing Yang; Siping Wei; Wenhai Wang; Hua Chen; Jingbo Lan

doi:10.1107/S1600536808004868

. 2008 Feb 27;64(Pt 3):o631. doi: 10.1107/S1600536808004868

(S)-2-(1H-Imidazol-1-yl)-3-phenylpropanol

Zuxing Yang ^a, Siping Wei ^a, Wenhai Wang ^a, Hua Chen ^a, Jingbo Lan ^a,^*

PMCID: PMC2960794 PMID: 21201962

Abstract

In the title compound, C₁₂H₁₄N₂O, the middle C atom in the propanol chain is a chiral center and possesses an S absolute configuration, according to the synthesis. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link the molecules into a chain along the b axis.

Related literature

For related literature, see: Bao et al. (2003 ▶); Baudequin et al. (2003 ▶); Lan et al. (2004 ▶); Matsuoka et al. (2006 ▶); Nair et al. (2004 ▶); Sambrook et al. (2005 ▶); Wang et al. (2007 ▶); You et al. (2001 ▶).

Experimental

Crystal data

C₁₂H₁₄N₂O
M _r = 202.25
Monoclinic,
a = 8.021 (4) Å
b = 6.069 (3) Å
c = 11.629 (5) Å
β = 90.13 (5)°
V = 566.1 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.40 × 0.33 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1909 measured reflections
1146 independent reflections
826 reflections with I > 2σ(I)
R _int = 0.055
3 standard reflections every 200 reflections intensity decay: 1.2%

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.090
S = 1.05
1146 reflections
142 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004868/ez2119sup1.cif

e-64-0o631-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004868/ez2119Isup2.hkl

e-64-0o631-Isup2.hkl^{(56.7KB, 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
O1—H1⋯N2ⁱ	0.82	1.98	2.802 (4)	177

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (grant No. 20602027) for financial support.

supplementary crystallographic information

Comment

Imidazoles are an important group in biological systems, and their derivatives have attracted widespread interest due to their application as precursors for imidazolium-based ionic liquids (Baudequin et al., 2003), N-heterocyclic carbenes (Nair et al., 2004) and molecular sensors (Sambrook et al., 2005). We have focused our interest on the synthesis and applications of imidazole derivatives (Lan et al., 2004; Wang et al., 2007) and have reported several chiral cyclophanes and chiral molecular tweezers containing imidazole residues as receptors for the enantioselective recognition of amino acids or their derivatives (You et al., 2001). Here, we report the crystal structure of the title compound, (I), which is a basic unit in the construction of chiral receptors and could be applied in the preparation of chair heterocyclic carbenes and ionic liquids.

In the structure of (I), the hydroxyl group and the imidazol-1-yl nitrogen atom are hydrogen bonded via an intermolecular O—H···N hydrogen bond as illustrated in Table 1 to result in the formation of a helical chain.

Experimental

Since enantiopure amines are easily available and the chiral carbon has little risk of the racemization, they are usually applied for the preparation of chiral imidazole derivatives by cyclocondensation of ring fragments (Matsuoka et al., 2006). The methyl 2-(1H-imidazol-1-yl)-3-phenylpropanoate was easily prepared according to a literature procedure (Bao et al., 2003). Thereafter, NaBH₄ (1.52 g, 40 mmol) was added to methyl 2-(1H-imidazol-1-yl)-3-phenylpropanoate (2.16 g, 10.0 mmol) in ethanol (150 ml) at 273 K over 30 min. The mixture was stirred at 333 K for another 20 h and then evaporated under vacuum. The residue was diluted with 20 ml saturated K₂CO₃ and extracted with 50 ml e thyl acetate. The organic layer was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with CH₂Cl₂/CH₃OH (20/1, V/V), and then recrystallized from CH₂Cl₂ to give colorless crystals. Yield: 86%, mp 359–361 K, ¹H NMR (300 MHz, CDCl₃): δ 2.94–3.17 (dd, J=13.8 Hz, 7.7 Hz, 2H), 3.78–3.88 (m, 2H), 4.13–4.29 (m, 1H.), 6.88 (m, 2H), 7.02 (m, 2H), 7.28 (s, 1H), 7.03–7.26 (m, 5H). ¹³C NMR (75 MHz, CDCl₃): δ 38.41, 62.26, 64.21, 117.61, 126.99, 128.59, 128.76, 128.90, 136.47, 137.10 p.p.m..