Citric Acid → HCID 54473341, compound

Participants

Reaction Steps

To 5,6-dihydro-8H-[1,2,4]triazolo[1,5-a]pyrazine-2,7-dicarboxylic acid 7-tert-butyl ester 2-ethyl ester (0.90 g, 3.0 mmol), in THF (20 ml) was added lithium borohydride (73 mg, 3.4 mmol), and the resultant mixture was stirred at room temperature overnight. Citric acid solution (10%, 25 ml) was added, then the mixture was washed with dichloromethane (2×50 ml). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate and then 5% methanol in ethyl acetate, yielding 2-hydroxymethyl-5,6-dihydro-8H-[1,2,4]triazolo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a colourless oil (330 mg). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 1.50 (9H, s), 2.41 (1H, br s), 3.93 (2H, t, J=5.3 Hz), 4.18 (2H, t, J=5.4 Hz), 4.74 (4H, s); MS (ES+) m/e 255 [MH]+.

Provenance & Evidence