Sodium borohydride → 3-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of nickel (II) chloride hexahydrate (12.2 mg, 0.05 mmol) and (E)-3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-acrylic acid methyl ester (100 mg, 0.26 mmol) in methanol (5 mL) was cooled to 0° C. and then treated with sodium borohydride (29 mg, 0.77 mmol). After the addition, the black reaction mixture was stirred for 15 min at 0° C. and then allowed to warm to 25° C. where it was stirred for 15 h. The reaction mixture was concentrated in vacuo, and the residue was diluted with a 3N aqueous hydrochloric acid solution (10 mL) and ethyl acetate (25 mL). The two layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution (1×25 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford racemic 3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid methyl ester (105 mg, 99%) as a viscous oil: EI-HRMS m/e calcd for C18H24N4O4S (M+) 392.1518, found 392.1526.

Provenance & Evidence