Sodium borohydride → HCID 67110511, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (8R,10aS)-6-chloro-3-[(4-methylphenyl)sulfonyl]-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one and (8R,10aS) -6-chloro-2-[(4-methylphenyl)sulfonyl]-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H) -one prepared as described in Step 1 (0.026 g, 0.059 mmol) was dissolved in 0.5 mL of ethanol, cooled to 0° C., and sodium borohydride (0.013 g, 0.34 mmol) was added. After 30 minutes, the reaction was quenched by addition of three drops of saturated NH4Cl, diluted with dichloromethane, and dried over MgSO4. The solution was filtered through a pad of silica gel, rinsing with EtOAc, and concentrated under reduced pressure to give (7R,8R,10aS)-6-chloro-3-[(4-methylphenyl)sulfonyl]-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol and (7R,8R,10aS)-6-chloro-2-[(4-methylphenyl)sulfonyl]-2,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol.

Provenance & Evidence