Carbon Tetrachloride → Benzo[1,2-b:4,3-b′]dipyrrole-1,6(3H)-dicarboxylic acid, 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)-2-(trifluoromethyl)-, 6-(1,1-dimethylethyl) 1-methyl ester

Participants

Reaction Steps

104.1 Milligrams (0.2 mmol) of methyl 5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate, and 104.9 mg (0.4 mmol) of triphenylphosphine were suspended in 1 ml of anhydrous acetonitrile. Thereto 115.3 μl (1.2 mmol) of carbon tetrachloride was added dropwise. The mixture was stirred for 5 hours under atmosphere of argon. After removal of the solvent, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain methyl 5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 106.7 mg (99%).

Provenance & Evidence