Sodium Azide → HCID 57509254, compound

Participants

Reaction Conditions

Reaction Steps

300 mg (2.14 mmol) of racemic 2-cyclohexyl-2-methyloxirane was dissolved in 40 mL Tris-SO4 buffer (200 mM, pH 7.5), followed by addition of purified enzyme (9 mg of halohydrin dehalogenase HheC in 280 μL buffer) and 69 mg (1.06 mmol) of NaN3. The reaction mixture was stirred at room temperature (24° C.) and monitored by gas chromatography (GC). The reaction was stopped after 2.5 h and extracted with 3×25 mL of ethylacetate. The combined organic phase was dried over Na2SO4 and 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 (155 mg, 51% yield, e.e. 76%) and (R)-azido-2-cyclohexylpropanol-2-ol (163 mg, 41% yield, e.e.>99%). 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