Triethylamine → HCID 59159287, compound

Participants

Reaction Steps

To a solution of 3-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionaldehyde (117 mg, 0.35 mmol) in EtOH (1.6 mL) and CH2Cl2 (1.6 mL) were added (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2; 70 mg, 0.43 mmol) triethylamine (43 mg, 0.43 mmol), borane pyridine complex solution (8 M in pyridine, 0.093 mL, 0.74 mmol), then after 1 h the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2, then CH2Cl2/MeOH 4:1) afforded the title compound (90 mg, 58%). Light yellow oil, MS: 442.3 (M+H)+.

Provenance & Evidence