Sodium borohydride → HCID 118389634, compound

Participants

Reaction Conditions

Reaction Steps

Cerium(III) chloride heptahydrate (62 mg, 0.167 mmol) was added to a solution of methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(3-oxocyclohex-1-en-1-yl)-1H-pyrazol-5-yl]acetate (43c) (63 mg, 0.139 mmol) in ethanol (0.46 mL). The reaction mixture was cooled to 0° C. and sodium borohydride (6 mg, 0.167 mmol) was slowly added. After stirring for 1 hour at the same temperature, the reaction was quenched with water (2 mL) and concentrated in vacuo to remove ethanol. The resulting aqueous layer was extracted with ethyl acetate (2×2 mL). The organic layer was washed with brine (3 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (dichloromethane/ethyl acetate 50/50) to provide methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(3-hydroxycyclohex-1-en-1-yl)-1-methyl-1H-pyrazol-5-yl]acetate (43d) (55 mg, 0.121 mmol, 87%) as a mixture of diastereoisomers.

Provenance & Evidence