O-Methylhydroxylamine hydrochloride → HCID 76541144, compound

Participants

Reaction Steps

Add N-[9-(3-fluoro-benzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 197) (crude, 506 mg, 1.29 mmol) to a suspension of methoxyamine hydrochloride salt (140 mg, 1.48 mmol) and pyridine (10 mL). Stir the reaction at ambient temperature for 12 h. Remove the pyridine under vacuum and dissolve the resultant residue in ethyl acetate (100 mL). Wash with saturated aqueous copper sulfate (2×50 mL) and water (2×50 mL). Separate the organic layer and dry over magnesium sulfate, filter, and concentrate under vacuum to give a greasy yellow solid. The solid was purified with column chromatography (silica gel; 10% to 50% ethyl acetate in hexanes) to give 183 mg (34%) of the title compound as a white solid. mp: 180-182° C.; ESI MS m/z 422 [C25H28FN3O2+H]+; 1H NMR (300 MHz, CDCl3) δ 8.28 (s, 1H), 7.79 (s, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.26-7.17 (m, 2H), 6.93 (t, J=7.1 Hz, 1H), 6.75 (d, J=7.6 Hz, 1H), 6.62 (d, J=9.1 Hz, 1H), 5.49 (br d, J=7.0 Hz, 1H), 5.24 (s, 2H), 4.40 (br s, 1H), 3.97 (s, 3H), 3.15 (dd, J=15.8, 4.7 Hz, 1H), 2.71-2.61 (m, 3H), 2.28 (septet, J=6.8 Hz, 1H), 2.07-2.00 (m, 2H), 1.14 (d, J=6.7 Hz, 3H), 1.12 (d, J=6.7 Hz, 3H).

Provenance & Evidence