Benzyl Bromide → (1R,7S)-3-benzyl-1,10,10-trimethyl-4-phenyl-3,4-diazatricyclo[5.2.1.02,6]dec-2(6)-en-5-one

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl bromide (0.54 mL, 4.5 mmol) and (4S,7R)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 1.11 g, 4.1 mmol) in N,N-dimethylformamide was heated at 78° C. for 2.5 h. The reaction mixture was diluted with 1 M NaOH (200 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 M NaOH and brine, dried (magnesium sulfate), filtered and evaporated. The residue was recrystallized from ethyl acetate/hexanes to give (4S,7R)-1-benzyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (114 mg, 8%) as a tan solid. APCI-MS (M+H) 359.

Provenance & Evidence