Ammonium Hydroxide → (3R,4R)-benzyl 4-amino-3-hydroxy-3-methylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (4.50 g, 19.29 mmol) and concentrated ammonium hydroxide (16 mL, 411 mmol) in dioxane (8 mL) in a sealed vessel was heated to 100° C. for 15 h. The resulting mixture was concentrated to afford (3R,4R)-benzyl 4-amino-3-hydroxy-3-methylpyrrolidine-1-carboxylate along with its regioisomer (4.8 g, 85:15 ratio), which was used in the next step without purification. MS (ES+) m/z: 218.2 (M+H).

Provenance & Evidence