Sodium borohydride → HCID 67490796, compound

Participants

Reaction Steps

To a cooled solution (−20° C.) of (3aS)-1-hydroxy-6-oxo-5-[(R)-1-phenylethyl]tetrahydrofuro[3,4-c]pyrrole-3a-carboxylic acid tert-butyl ester (350 mg, 1.01 mmol) in tetrahydrofuran and ethanol (10 mL; 4:1), sodium borohydride (38.0 mg, 1.00 mmol) was added portionwise, and the mixture was stirred at the same temperature for 5.5 h. The reaction mixture was concentrated in vacuo and taken up in AcOEt and water. The layers were separated and the aqueous layer extracted with AcOEt. The combined extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 90% AcOEt in hexane to afford the title compound (153 mg) as a colorless oil.

Provenance & Evidence