Sodium borohydride → HCID 67275569, compound

Participants

Reaction Conditions

Reaction Steps

The crude 2-cyclopropyl-1-{5-[(cyclopropylmethyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}ethanone (817 mg, 3.25 mmol) was dissolved in methanol (20 mL) and the mixture cooled in an ice bath (4° C.). Sodium borohydride (285 mg, 7.5 mmol) was added portionwise and the reaction mixture stirred at 4° C. for 30 min and then at room temperature for 2 h. Solvent was removed in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate to give the title compound (578 mg, 24% yield over 2 steps). 1H NMR (500 MHz, CDCl3) δ (ppm) 4.91 (1H, s), 3.75 (1H, s), 3.65 (3H, s), 3.11 (2H, d, J=7.3 Hz), 1.98-1.90 (1H, m), 1.84-1.78 (1H, m), 1.20-1.12 (1H, m), 0.88-0.80 (1H, m), 0.62-0.58 (2H, m), 0.53-0.43 (2H, m), 0.29-0.26 (2H, m), 0.18-0.12 (1H, m), 0.08-0.04 (1H, m).

Provenance & Evidence