Ammonia → HCID 11738220, compound

Participants

Reaction Steps

Sodium metal (513 mg, 22.5 mmol) was added in portions during 5 min. to a solution of 4-(3-Benzylsulfanyl-2-carboxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.9 g, 2.29 mmol) in THF (45 mL) and liquid ammonia (50 mL) at −60° C. under argon. After stirring for 15 min. ammonium chloride (1.7 g, 31.5 mmol) was added in portions. The cooling bath was removed and the ammonia was evaporated using a stream of argon. 0.5 M NaOH was added and the mixture was washed with heptane. The aqueous phase was acidified with 2 M HCl and extracted with methylene chloride. The organic phase was washed with brine, dried and concentrated under reduced pressure to give 4-(2-Carboxy-3-mercapto-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.7 g, 100%).

Provenance & Evidence