Water → cis-3-Hydroxymethyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To ester 6 (1.50 g; 5.29 mmol) in ethanol (50 mL) at 0° C., was added sodium borohydride (1.57 g; 41.5 mmol) in several portions. The reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature for 3 hours. The reaction mixture was carefully added to water (150 mL) and extracted with methylene chloride (3×100 mL). The combined organic layers were washed with several portions of water, brine, dried (MgSO4), filtered and evaporated to yield alcohol 7 as a white solid.

Provenance & Evidence