Methanol → 7-Hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 8-methoxy-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid methyl ester (1.51 g, 4.27 mmol) in dry DCM (50 mL), cooled to −78° C., was added 1 M DIBAL in DCM (8.54 mL, 8.54 mmol) over 3 minutes. The reaction mixture was allowed to warm to −50° C. over 45 minutes, followed by cooling to −78° C. and addition of MeOH (5 mL) to quench the reaction. The reaction mixture was allowed to warm to 0° C. and was diluted with DCM. An aqueous solution of Rochelle salt (200 mL, 10% w/v) was added and the mixture was stirred vigorously for 30 minutes. The aqueous phase was isolated and extracted with DCM. The combined organic phases were washed with water, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 50 to 100% EtOAc in cyclohexane) to afford the title compound (1.23 g, 89%) as a pale yellow solid. LCMS (Method A): RT=4.18 min, [M+H]+=326.

Provenance & Evidence