Ethanol → HCID 86606465, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 31 (288 mg, 0.587 mmol, 31a:31b=ca. 1:2) in EtOH (1 mL) cooled to 0° C. was added NaBH4 (26.6 mg, 0.704 mmol). After, the reaction mixture was stirred for 1 h at 0° C., into the reaction mixture was poured ice water, and extracted with AcOEt. The organic layer was washed with saturated brine, and dried over anhydrous MgSO4. Solvents were removed in vacuo, and the residue was purified by silica gel column chromatography (10 g; 15% AcOEt/hexane) to yield Compound 32 (283.3 mg, 98%) as a mixture of two stereoisomers. The ratio of the stereoisomers constituting the mixture was ca. 2:1. It was impossible to know whether the major product was aS*,2R,6R isomer or aR*,2R,6R isomer.

Provenance & Evidence