Sodium borohydride → HCID 70161399, compound

Participants

Reaction Steps

Sodium borohydride (36 mg) was added to a solution of 400 mg of ethyl (Z)-3-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-3-oxopropionate in 10 ml of tetrahydrofuran-ethanol (1:1), and the mixture was stirred at room temperature for 28 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated aqueous solution of NaCl and dried over magnesium sulfate, and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform-methanol). The resulting residue was collected by filtration to give 300 mg of (Z)-1-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)propane-1,3-diol (29a) as a colorless amorphous solid and 90 mg of ethyl (Z)-3-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-3-hydroxypropionate (29b) as a colorless amorphous solid.

Provenance & Evidence