Sodium Hydroxide → Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-2,3-dihydro-1H-indole-5-yloxy]-butyl}-methyl-amine

Participants

Reaction Steps

A solution of 25 mg (0.67 mol) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-methyl-amine in 1 ml AcOH/TFA (1:1) was treated at 0° C. with 70 mg (1.11 mmol) NaBCNH3 and stirred at room temperature for 8 hours. The mixture was poured into icy 2M NaOH and extracted three times with Et2O. Evaporation of the solvent, drying with MgSO4 and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1 gave 20 mg (80%) Allyl-{4-[1-(4-chloro-phenyl)-6-fluoro-2,3-dihydro-1H-indole-5-yloxy]-butyl}-methyl-amine, MS: 389 (MH+).

Provenance & Evidence