Sodium Azide → HCID 24865700, compound

Participants

Reaction Conditions

Reaction Steps

500 mg (5.8 mmol) of racemic 2-ethyl-2-methyloxirane was dissolved in 100 mL Tris-SO4 buffer (200 mM, pH 7.5), followed by addition of purified enzyme (15 mg of halohydrin dehalogenase HheC in 450 μL buffer) and 189 mg (2.9 mmol) NaN3. The reaction mixture was stirred at room temperature (24° C.) and monitored by gas chromatography (GC). The reaction was stopped after 1 h and extracted three times by adding 50 mL ethylacetate. The combined organic phases were dried over Na2SO4 and evaporated. The crude product was chromatographed on a silica gel 60 H using pentane/CH2Cl2 (4:6) as eluent. This yielded pure (S)-2-ethyl-2-methyloxirane (205 mg, 41% yield, e.e.>99%) and (R)-azido-2-methylbutan-2-ol (320 mg, 43% 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