Acetic Acid → HCID 86756045, compound

Participants

Reaction Steps

To a stirred solution of (1RS,3RS,5RS)-3-[{5-(1,2,4-triazol-4-yl)-1H-indol-3-yl}methyl]-2,7-diazabicyclo[3.3.0]octane-7-carboxylic acid, ethyl ester (1.6514 g, 4.34 mmol) in methanol (70 mL) was added glacial acetic acid (0.99 mL, 17.3 mmol), 37% solution of formaldehyde in water (0.423 mL, 5.64 mmol) and sodium cyanoborohydride (0.3309 g, 5.27 mmol). The mixture was stirred at room temperature under argon for 3.5 h before quenching with saturated K2CO3 solution (200 mL) and extracting with EtOAc (3×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2 --MeOH--NH3 (aq); 95:5:0.5 then 94:6:0.6) to give 1.4723 g (86.0%) of the title compound as a cream solid. δH (250 MHz, CDCl3) 1.23 (3H, t), 1.63 (1H, m), 1.84-1.96 (1H, m), 2.52 (3H, s), 2.59 (1H, m), 3.78 (1H, m), 4.10 (2H, q, J=7.0 Hz), 7.14-7.20 (2H, m), 7.50 (1H, d, J=12.6 Hz), 7.52 (1H, s), 8.48 (2H, s), 8.63 (1H, br s). m/e (ES+) 395 (M+H)+.

Provenance & Evidence