Acetic Acid → (2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate

Participants

Reaction Steps

(S)-tert-Butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate (15) (4.0 g, 17.62 mmol) was dissolved in CH2Cl2 (90 mL) and acetic acid (10 mL) and cooled to 0° C. NaBH4 (1.33 g, 35.24 mmol) was added in several portions and the reaction stirred for 16 hr at rt. EtOAc (300 mL) was added and the organics were washed with sat. aq. NaHCO3 (300 mL), brine (200 mL), and dried over Na2SO4. Concentration of the solution in vacuo led to isolation of (2S,3R)-tert-butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate (16) (1.34 g, 33%) as a white solid.

Provenance & Evidence