Water → Benzyl carbamate

Participants

Reaction Steps

A sample of (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (72 g) was dissolved in CH2Cl2 (750 mL) prior to the addition of CDI (50.9 g). After 2.5 h water was added, and the solution was extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated. The resulting material was dissolved in CH2Cl2 and ammonia gas was bubbled through the solution for 1.5 h. After stirring overnight, the majority of the solvent was removed and Et2O was added. The product precipitated as a white solid and was collected to give (1R,6S)-6-carbamoylcyclohex-3-enyl)carbamic acid benzyl ester (61.5 g). MS found: (M+H)+=275.3.

Provenance & Evidence