Ethanol → HCID 11054718, compound

Participants

Reaction Steps

tert-Butyl (2S,3R)-4-chloro-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (1 g, 3.28 mmol) was dissolved in a solution of 0.7 N NaOH in EtOH (5.6 mL, 3.95 mmol, 1.2 eq). After stirring for 1 h, the mixture was concentrated to give the residue, which was dissolved in water, extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl (S)-2-cyclohexyl-1-((R)-oxiran-2-yl)ethylcarbamate (0.83 g, 95%). 1H NMR: 0.85 (m, 1H), 0.99 (m, 1H), 1.12-1.32 (m, 3H), 1.41 (m, 3H), 1.45 (s, 9H), 1.58 (m, 4H), 1.88 (m, 1H), 2.59 (m, 1H), 2.73 (m, 1H), 2.98 (m, 1H), 4.04 (m, 1H), 4.32 (m, 1H). MS (E/Z): 270 (M+H+).

Provenance & Evidence