Cyanomethylenetributylphosphorane → 3-[5-(4-Isopropyl-piperazine-1-carbonyl)-indol-1-ylmethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 21.7 mg (0.08 mmol) (1H-indol-5-yl)-(4-isopropyl-piperazin-1-yl)-methanone (intermediate 1), 24.1 mg (0.12 mmol) 3-Hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (commercially available), 38.6 mg (0.16 mmol) cyanomethylenetri-n-butylphosphorane in 1.5 mL toluene was heated to 110° C. for an extended period of time. After evaporation the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 14.3 mg of the title compound. MS(m/e): 455.4 (MH+).

Provenance & Evidence