Sodium cyanoborohydride → Methyl 3-[N-(p-Chlorobenzyl)-3-benzyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-(benzoyloxy)indol-2-yl]-2,2-dimethylpropanoate (360 mg) (prepared in Step A of Example 9), 800 mg of ZnI2, and 500 mg of sodium cyanoborohydride were stirred in 5 mL of dichloroethane at RT under argon for 30 min. The temperature was then raised to 65° C. for 3 hr. After the solution had cooled, it was poured onto 10 mL of NH4OAc (25% solution), extracted with 3×15 mL of ether, washed with 10 mL of H2O and dried (MgSO4). The solution was evaporated to dryness and the residue was chromatographed on silica gel to yield the title compound as a white foam.

Provenance & Evidence