Hydrogen Peroxide → HCID 66674539, compound

Participants

Reaction Steps

Borane-dimethylsulfide complex (2M solution in THF, 1.6 eq) was added to a solution of methyl 14-cyclohexyl-7-methylene-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (from Step 1) in dry THF (0.12 M) at 0° C. The solution was stirred for 16 h at RT. The reaction mixture was cooled to 0° C. and treated dropwise with 3N NaOH (3 eq.) followed by 35% (v/v) H2O2 solution and the resulting mixture was stirred for 2 h at RT. The mixture was diluted with EtOAc, washed with aqueous saturated NaHCO3-solution and with brine, dried (Na2SO4). Evaporation afforded a crude residue which was purified by flash chromatography (4:1 PE/EtOAc). Methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (50%) was obtained as colorless solid; MS (ES+) m/z 402 (M+H)+.

Provenance & Evidence