Sodium Cyanide → HCID 57509254, compound

Participants

Reaction Conditions

Reaction Steps

200 mg (1.42 mmol) of racemic 2-cyclohexyl-2-methyloxirane was dissolved in 25 mL Tris-SO4 buffer (200 mM, pH 7.5), followed by addition of purified enzyme (9 mg of halohydrin dehalogenase HheC in 1.2 ml buffer) and 35 mg (0.71 mmol) NaCN. The reaction mixture was stirred at room temperature (24° C.) and monitored by gas chromatography (GC). The reaction was stopped after 24 h and extracted three times with 15 mL ethylacetate. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product was chromatographed on a silica gel 60 H using pentane/CH2Cl2 (4:6) as eluent, which yielded pure (S)-2-cyclohexyl-2-methyloxirane (105 mg, 52% yield, e.e. 71%) and (S)-3-cyclohexyl-3-butanenitrile (95 mg, 40% yield, e.e. 100%). Optical purities were determined by GC using a Chiraldex G-TA column (30 m×0.25 mm×0.25 μm). The NMR data were identical with those of synthesized racemic reference compounds.

Provenance & Evidence