Sodium borohydride → HCID 86722349, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2′R,4aS,12bS)-9-(4-fluorophenyl)-12b-(pyridin-2-ylmethyl)-2,4,4a,5,6,7,9,12b-octahydro-1H-spiro[benzo[6,7]cyclohepta[1,2-f]indazole-3,2′-oxirane]compound with (2′S,4aR,12bR)-9-(4-fluorophenyl)-12b-(pyridin-2-ylmethyl)-2,4,4a,5,6,7,9,12b-octahydro-1H-spiro[benzo[6,7]cyclohepta[1,2-f]indazole-3,2′-oxirane] (12, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (500 mg, 1.10 mmol) in EtOH (10 mL) was treated with NaBH4 (104 mg, 2.76 mmol). The reaction was warmed to 60° C. for about 20 min and then allowed to stir at rt for about 18 h. The reaction was concentrated under reduced pressure, then sat. aq. NH4Cl (25 mL) was added and the product was extracted with EtOAc (2×25 mL). The organic solution was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified on silica gel (25 g) using EtOAc as eluent. Product fractions were combined and concentrated to yield (3R,4aS,12bS)-9-(4-fluorophenyl)-3-methyl-12b-(pyridin-2-ylmethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-3-ol; compound with (3S,4aR,12bR)-9-(4-fluorophenyl)-3-methyl-12b-(pyridin-2-ylmethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-3-ol (13, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl, R3=Methyl) (503 mg, 100%) as a white solid.

Provenance & Evidence