4-Toluenesulfonyl chloride → toluene-4-sulfonic acid (1R,2R)-2-benzyloxycarbonylamino-cyclohexylmethyl Ester

Participants

Reaction Steps

A solution of (1R,2R)-(2-hydroxymethylcyclohexyl)-carbamic acid benzyl ester (6.0 g, 22.8 mmol) in pyridine (35 mL) was stirred on an ice-acetone bath and treated with toluene-4-sulfonyl chloride (4.78 g, 25.1 mmol). The reaction was stirred on an ice-water bath for 3 hours, then ice-cold water (35 mL) was added slowly. The mixture was diluted further with ice water and the resulting slurry was stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water, and dried under vacuum to provide a white powdery solid (9.1 g, 96%).

Provenance & Evidence