Triethylamine → HCID 70154690, compound

Participants

Reaction Steps

A solution of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)cyclohexaneacetic acid, benzyl ester (35 mg, 0.086 mmol; prepared above as Aldehyde 4), 4-(N-(pyrid-3-yl)-N-allylamino)piperidine dihydrochloride (28 mg, 0.103 mmol, from Step B), sodium triacetoxyborohydride (44 mg, 0.206 mmol) and triethylamine (0.03 mL, 0.206 mmol) were stirred in 2 mL 1,2-dichloroethane for 12 h. The mixture was diluted with 25 mL EtOAc and washed with water and sat'd aq. NaCl. The organic phase was dried over Na2SO4 and concentrated. Flash chromatography (5 grams silica, 0→2% MeOH/CH2Cl2 eluent) afforded 37 mg (70%) of the title compound. M/z; (M+H)=607.4 (obs), 607.4 (calc.).

Provenance & Evidence