Water → HCID 59383020, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethylsilyloxy)-cyclohexyl)propan-1-ol (23 g, 59 mmol) in CH2Cl2 (250 mL) was added Et3N (15 g, 148 mmol). The reaction mixture was cooled to −20° C. and a solution of MsCl (14.9 g, 131 mmol) in CH2Cl2 (40 mL) added dropwise. After returning to rt then stirring for an additional 1 h, at which point TLC showed no starting material, water (100 mL) was added and the mixture was extracted with CH2Cl2 (2×150 mL). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give crude (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethyl-silyloxy)cyclohexyl)-1-methanesulfonyloxypropane (30 g) that was used in the next step without further purification.

Provenance & Evidence