(S)-5-Oxopyrrolidine-2-carboxamide → (S)-5-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

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Reaction Steps

A THF solution of 11A pyroglutamide (3.9 g, 11 mmol) is chilled to −78° C. After 15 minutes, 1 M super-hydride solution (13 mL, 13 mmol) is slowly added. After 1 hour, it is carefully quenched with saturated bicarb and added 4 mL 30% hydrogen peroxide and concentrated to half volume and reconstituted with ethyl acetate, then washed with saturated bicarb and brine and dried over anhydrous sodium sulfate, filtered and concentrated to a clear oil. LCMS characterization ES+369.1 (m+1).

Provenance & Evidence