Piperidine → (R)-4-(3,4-dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(piperidin-1-ylmethyl)phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3.4-dihydropyrazin-2(1H)-one

Participants

Reaction Steps

To a solution of 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetra-hydropyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzaldehyde (0.150 g, 0.288 mmol) and piperidine (0.10 mL, 1.01 mmol) in 1,2-dichloroethane (10 mL) was added NaBH(OAc)3 (0.126 g, 0.594 mmol). After 18 h, the solution was diluted with 60 mL EtOAc and washed with 5% NaHCO3 (60 mL×2), brine (60 mL×2), dried over Na2SO4 and concentrated under reduced pressure. The crude product was chromatographed on SiO2 (100% CH2Cl2 to 5% 2N methanolic NH3 in CH2Cl2) to yield the title compound.

Provenance & Evidence