Sodium Hydroxide → Benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate

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Reaction Steps

benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (10.5 g) was stirred in 200 ml of saturated ammonium hydroxide at 35° C. for 40 h. The reaction mixture was poured into 100 ml of 2 N NaOH, extracted methylene chloride (4×200 ml), dried MgSO4, filtered and concentrated to provide the title compound as an oil (10.15 g, 95%): 1H NMR (300 MHz, CDCl3) δ) 7.34, 5.14, 3.99, 3.78, 3.37, 3.19, 1.77; HRMS (FAB) calcd for C12H16N2O3+H 237.1239, found 237.1244.

Provenance & Evidence