4-Chlorobenzenesulfonyl chloride → HCID 69471349, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,5S)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine (0.98 g, 3.9 mmol) in ClCH2CH2Cl (5 mL) was added 1.9 mL (13.7 mmol, 3.5 eq) of Et3N and 1.45 g (6.86 mmol, 1.8 eq) of 4-chlorobenzenesulfonyl chloride. The mixture was heated at 70° C. for 16 hr. After cooling to room temperature, the mixture was diluted with CH2Cl2 (20 mL), washed with water (10 mL), saturated brine (10 mL), dried (Na2SO4) and concentrated under vacuum. The crude product was chromatographed on silica gel (2% EtOAc/hexane) to give 0.78 g (46%) of (2R,5S)-1-(4-chloro-benzenesulfonyl)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine as a yellow gum.

Provenance & Evidence