7-N-(tert-Butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8 tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine → 7-N-(tert-Butoxycarbonyl)-8-(hydroxymethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Participants

Reaction Steps

To a solution of 733 mg (1.8 mmol) of 7-N-(tert-butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine in 8.0 mL of ethanol was added 400 mg of 10% palladium on carbon. The mixture was stirred under an atmosphere of hydrogen for 29 h. TLC analysis indicated that starting material was present. Thus 400 mg of 10% palladium on carbon was added and the mixture shaken on a Parr apparatus under 42 psi hydrogen for 12 h. The reaction mixture was filtered through Celite and concentrated. Flash chromatography (silica gel, 7% to 50% ethyl acetate/hexane gradient) gave the title compound as a white solid. LC/MS 267 (M+1-tBu).

Provenance & Evidence