HCID 68954276, compound → Methyl 3-benzyloxy-7-hydroxymethyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Participants

Reaction Steps

To a solution of 3-benzyloxy-2-methoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-7-carboxylic acid (183 mg, 0.509 mmol) in anhydrous THF under an atmosphere of nitrogen was added 1M borane-THF complex (6.11 mL, 6.11 mmol). The reaction was stirred at room temperature for 1 hour and quenched with aqueous 6N HCl. The solvent was removed in vacuo, and the resulting residue was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the alcohol as a sticky, clear oil. 1H NMR (400 MHz, d6-DMSO) δ 7.49-7.47 (m, 2H), 7.39-7.30 (m, 3H), 5.18 (s, 2H), 4.50-4.47 (m, 1H), 4.27 (br s, 1H), 4.07 (dd, J=5.2, 13.6 Hz, 1H), 3.91 (dd, J=5.2, 13.2 Hz, 1H), 3.79 (s, 3H), 3.78-3.71 (m, 2H), 3.03 (s, 3H); ES MS (M+H)=346.

Provenance & Evidence