反应详情

tert-Butyl (2S,3S)-4-chloro-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (1 g, 3.28 mmol) was dissolved in a solution of 0.71 N NaOH in EtOH (5.6 mL, 3.95 mmol, 1.2 eq). After stirring for 1 h, the mixture was concentrated to give a residue, which was dissolved in water and 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-((S)-oxiran-2-yl)ethylcarbamate (0.84 g, 95%). 1H NMR: 0.83 (m, 1H), 0.95 (m, 1H), 1.10-1.42 (m, 5H), 1.45 (s, 9H), 1.68 (m, 5H), 1.76 (m, 1H), 2.72 (m, 2H), 2.83 (m, 1H), 3.55 (m, 1H), 4.38 (m, 1H). MS (E/Z): 270 (M+H+).

1. concentrationthe mixture was concentrated
2. customto give a residue, which
3. extractionextracted with EtOAc (3×15 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo