Sodium → (3S)-3-(Cyclobutyl-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Add sodium borohyride (1.19 g, 31.4 mmol) to a stirred solution of (S)-3-cyclobutanecarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester (5.30 g, 20.9 mmol) in MeOH (105 mL) kept under an atmosphere of nitrogen at 0° C. Stir the mixture for 2 hours while warming to room temperature. Concentrate the MeOH, dilute with dichloromethane and wash the organics with saturated aqueous NaHCO3, water and brine. Dry (MgSO4), filter and concentrate under reduced pressure to yield the title compound (4.4 g, 82%) as a mixture of diastereomers (S-mix).

Provenance & Evidence