Isobutanol → HCID 10145143, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask fitted with a reflux condenser and a thermometer were introduced (2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetic acid (compound 235, 0.5 g, 0.84 mmoles) dissolved in THF (20 ml). To this solution cooled at 0° C. were successively added isobutanol (0.155 ml, 1.68 mmoles), DMAP (0.01 g, 0.084 mmoles) and EDCI (0.177 g, 0.93 mmoles). The reaction mixture was stirred for 2 hours at 0° C. and then allowed to reach room temperature and stirred overnight. The organic solution was washed with HCl 0.1N and water, dried over MgSO4 and concentrated. The resulting oil was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 99.5/0.5/0.1 v/v/v) to yield (2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetic acid isobutyl ester (compound 287, 390 mg, 65%) which was converted into its dihydrochloride monohydrate salt by reaction with HCl in diethylether.

Provenance & Evidence