Chloroform → (1S)-3-(3-chlorophenyl)-3-cyano-1-(2-[(phenylmethyl)oxy]ethyl}propyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of (4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile (6.00 g, 18.2 mmol) in 50% CHCl3 in pyridine at 0° C. was added DMAP (2.22 g) and toluenesulfonyl chloride (10.4 g, 54.5 mmol). After warming to room temperature over several hours, the reaction mixture was stored in the freezer for 2 days. After an aqueous work up with 1N HCl the organic layer was dried over MgSO4 and evaporated to an oil. Chromatography on silica with 25% EtOAc in Hexanes afforded the title compound (5.68 g, 66%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.9 (m, 2H) 2.1 (m, 2H) 2.3 (m, 2H) 2.4 (s, 3H) 3.4 (m, 1H) 3.5 (m, 1H) 4.4 (m, 2H) 7.1 (m, 1H) 7.3 (m, 10H) 7.8 (m, 2H)

Provenance & Evidence