Sodium Hydroxide → HCID 9946011, compound

Participants

Reaction Steps

A freshly prepared solution of sodium cyanoborohydride (0.91 g, 14.48 mmol) in CH3OH (3.0 mL) was added dropwise to a 0° C. solution of (3R)-9-methyl-6-(phenylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine (1.02 g, 2.99 mmol) in TFA (7.5 mL), then stirred at room temperature for 3 hours. The reaction was diluted with H2O (40 mL) cooled to 0° C. and made basic by the addition of 50% NaOH. The reaction mixture was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to give a colorless foam which was recrystallized from CH3OH/EtOAc to give 0.19 g (19%) of (3R)-9-methyl-6-(phenylsulfonyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazol-3-amine as a colorless as a mixture of cis and trans isomers: mp 217.0-219.3° C.; MS m/z 343.2 (M++H).

Provenance & Evidence