Triethylamine → (S)-1-(4-chlorophenethyl)-3-methanesulfonyloxypyrrolidine

Participants

Reaction Steps

(S)-1-(4-Chlorophenethyl)-3-hydroxypyrrolidine (190 mg, 0.84 mmol) was dissolved in dichloromethane (6 ml). Triethylamine (110 mg, 1.09 mmol) and methanesulfonyl chloride (125 mg, 1.09 mmol) were added to the obtained solution under stirring under cooling on ice. They were stirred at 0° C. for 1 hour. The reaction liquid was distributed in dichloromethane and water. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. The product was eluted with dichloromethane and then with a solvent mixture of dichloromethane and methanol (50:1). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure to obtain (S)-1-(4-chlorophenethyl)-3-methanesulfonyloxypyrrolidine in the form of a light yellow oil (252 mg, 99%).

Provenance & Evidence