Sodium Hydroxide → Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (110 g, 0.595 mol) in MeOH/water (1200 mL/200 mL) were added NaN3 (77.6 g, 1.19 mol) and NH4Cl (32 g, 0.598 mol). The resulting mixture was stirred at 60° C. overnight. NaOH (0.5 N, 200 mL) was added and the mixture was concentrated to remove MeOH. The residue was extracted with CH2Cl2 (3×400 mL) and the combined organic extracts were washed with water, brine, dried over Na2SO4, and then concentrated to give the title compound as a yellow liquid (quantitative yield). Used as is in next step.

Provenance & Evidence