Sodium borohydride → HCID 57108154, compound

Participants

Reaction Steps

A mixture of sodium borohydride (0.25 g, 6.61 mmol) and ethanol (5 mL) was stirred 10 min and then 7-benzyloxy-6-methyl-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one (0.30 g, 0.653 mmol in 20 mL of ethanol and 15 mL of tetrahydrofuran) was added. The reaction was stirred at ambient temperature overnight. Additional sodium borohydride (0.12 g) was added and stirring was continued over the weekend. The reaction was quenched with water and concentrated. The residue was triturated with water and filtered to give a solid which was a 2:1 mixture of starting material and product. This material was stirred with hot ethanol and filtered. The solid which was collected weighed 0.2 g and was pure starting material which could be recycled in this reduction step. The ethanol filtrate was concentrated to afford 0.113 g of (3R*,4S*)-7-benzyloxy-6-methyl-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chroman-4-ol which had: mp 201-202° C. This material was carried directly to the next step.

Provenance & Evidence