Methanol → HCID 137231142, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 2′-formyl-7′H-spiro[azetidine-3,5′-furo[3,4-b]pyridine]-1-carboxylate (0.5 g, 1.7 mmol, 1 eq.) in mixture of methanol (12 mL):water (12 mL) was added NaOAc (0.28 g, 3.45 mmol, 2 eq.) followed by addition of NH2OH.HCl (0.24 g, 3.45 mmol, 2 eq.) at room temperature. Resulting reaction mixture was stirred at room temperature for 18 hours under nitrogen atmosphere. After complete consumption starting material, reaction mixture was concentrated under reduced pressure; resulting residue was diluted with water (50 mL) and extracted by ethyl acetate (3×100 mL). Combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford title compound as brown solid (0.520 g, 99%). 1H NMR (400 MHz, CDCl3) δ: 1.47 (s, 9H), 4.12 (d, J=9.88 Hz, 2H), 4.34 (d, J=10.12 Hz, 2H), 5.08 (s, 2H), 7.73 (d, J=7.92 Hz, 1H), 7.79 (d, J=7.96 Hz, 1H), 8.21 (s, 1H). LC-MS (m/z): 306.3 (M+H).

Provenance & Evidence