Methyl 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetrahydro-pyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzoate → (R)-4-(3,4-Dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(hydroxymethyl)-phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

Methyl 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetrahydro-pyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzoate (1.38, 2.51 mmol) was dissolved in CH2Cl2 (200 mL) and cooled to −78° C. under N2. Dibal (1.5M solution in toluene, 8.4 mL, 12.6 mmol) was then added over 10 min. After 30 min, the cold bath was removed and the reaction was stirred for 4 h. To the solution was added MeOH (20 mL), followed by Na2SO4 (25.1 g) and saturated NH4Cl (2.5 mL). The reaction mixture was stirred overnight. The solids were removed by filtration, and washed with CH2Cl2/MeOH (10/1). The filtrate was concentrated and the residue was chromatographed on silica (100% CH2Cl2 to 5% MeOH in CH2Cl2) to yield the title compound.

Provenance & Evidence