Methylamine → Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dissolve 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1.50 g, 8.10 mmol) in methylamine (15 mL, 40% solution in water). Warm to 50° C. and stir in a sealed vessel overnight. Dilute the mixture with saturated sodium bicarbonate and extract with dichloromethane (3×). Dry the organics over sodium sulfate, filter, and evaporate. Purify by silica gel chromatography, eluting with 0-10% methanol (2N NH3)/CH2Cl2 to give 1.87 g (97%) of 3-hydroxy-4-methylamino-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil.

Provenance & Evidence