Diisopropylethylamine → HCID 178456100, compound

Participants

Reaction Steps

To a stirred solution of (R)-methyl 3-hydroxypentanoate (49.6 mg, 48.2 μl) in dioxane (3 ml) was added at room temperature potassium trimethylsilanolate (64.2 mg, 0 5 mmol) and the mixture was allowed to stir for additional 18 h. Afterwards N,N-diisopropylethylamine (178 mg, 1.38 mmol), trans-4-[2-(4-benzofuran-3-yl-piperidin-1-yl)-ethyl]-cyclohexylamine dihydrochloride (intermediate A) (100 mg, 0.25 mmol) and TBTU (121 mg, 0.376 mmol) were added, and the mixture was allowed to stir for 3 h at room temperature. The reaction mixture was poured into saturated NaHCO3 solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude material (130 mg) was further purified by flash chromatography on silica gel (dichloromethane/MeOH/NH4OH 150:10:1) to yield the title compound as white solid (95 mg, 89%), MS (ISP) m/z=427.3 [(M+H)+], mp 142° C.

Provenance & Evidence