Ammonia → (3R)-1-benzylpyrrolidin-3-amine

Participants

Reaction Steps

An autoclave was cooled with an acetone/dry ice bath, and an ammonia gas was blown to pool 64 cc of liquid ammonia (corresponding to 25 equivalent of (S)-1-benzyl-3-(methanesulfonyloxy)pyrrolidine). Thereto were added 30 g of (S)-1-benzyl-3-(methanesulfonyloxy)pyrrolidine (108.4 mmol, optical purity: 100% e.e.) and 118 g of methanol, which was heated to 100° C. whereby an internal pressure of 10 barr was observed. After allowing the reaction for 7 hrs, the reaction mixture was cooled to room temperature, and ammonia and methanol were removed by distillation under reduced pressure. As the residue, 26.6 g of a pale yellow oily material was obtained (reaction yield: 67%, optical purity: 85.8% e.e.).

Provenance & Evidence