Potassium Hydroxide → (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

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Reaction Steps

N-Cbz-3-(S)-amino-1-chloro-4-phenyl-2(S)-butanol (9.5 gm, 28 mmol) was added to a solution of KOH (1.9 gm, 34 mmol) in absolute ethanol (250 mL). After 15 minutes the solvent was removed and the residue dissolved in CH2C12 (100 mL). The organic solution was washed with water (100 mL) and dried (MgSO4). Filtration and concentration afforded a white solid, 7.4 gm (87%). Anal. Calc'd for C18H19NO3 : C, 72.71; H, 6.44; N, 4.71. Found: C, 72.16; H, 6.42; N, 4.65.

Provenance & Evidence