Ammonia → HCID 15117247, compound

Participants

Reaction Steps

In a flask purged with ammonia gas, about 40 mL of liquid ammonia is collected with ammonia condenser at −78° C. To the liquid ammonia is added portionwise lithium metal (46 mmol; 320 mg) at the same temperature. To the deep blue solution is added a solution of (2S,4R)-4-benzyloxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (9.2 mmol; 3.1 g) and tert-butanol (18.4 mmol; 1.36 g) in THF (15 mL). After stirring for 2 hours, the reaction mixture is quenched with MeOH, and then warmed to ambient temperature. The mixture is diluted with water, and then aqueous 1M HCl is added to reach pH 8-9. The product is extracted three times with EtOAc. The combined organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give (2S,4R)-4-hydroxy-2-methoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2.2 g).

Provenance & Evidence