(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester → (R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

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Reaction Steps

(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (30 g, 140.6 mmol, 1.0 eq.) was combined with (S,S)-Salen Co(II) (418 mg, 0.7 mmol). Water (⅓ mL) was added and the resulting mixture was stirred vigorously for 6 hours. Hexanes (200 mL) was added. The resulting solids were crushed and stirred in hexanes to yield a yellow precipitate. The precipitate was purified by column chromatography (200-300 mesh, hexanes:EtOAc=1:3, 3 L) to yield (R)—(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester.

Provenance & Evidence