Acetic Acid → HCID 90388177, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of Example 6a (0.015 g, 0.044 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (0.017 g, 0.087 mmol) was added dichloroethane (1 mL) and acetic acid (0.03 mL, 0.524 mmol). The reaction mixture was heated at 50° C. for 2 hours, treated with sodium triacetoxyhydroborate (0.028 g, 0.131 mmol) and heated overnight at 50° C. Additional tert-butyl 4-oxopiperidine-1-carboxylate (0.017 g, 0.087 mmol) was added and the mixture was heated for 1 hour. Additional sodium triacetoxyhydroborate (0.028 g, 0.131 mmol) was added and the mixture was heated over a second night at 50° C. The reaction mixture was cooled to ambient temperature, partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0-6% methanol in dichloromethane) to give 0.0194 g (84%) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ 10.71 (d, J=5.49 Hz, 1H), 7.69 (s, 1H), 7.64 (s, 1H), 7.13 (s, 1H), 6.79 (d, J=5.49 Hz, 1H), 4.40 (m, 2H), 4.11 (s, 3H), 3.87 (m, 2H), 3.73 (m, 1H), 3.63 (m, 1H), 3.19 (m, 1H), 2.91 (s, 3H), 2.66 (m, 2H), 1.67 (m, 1H), 1.58 (m, 1H), 1.45 (m, 2H), 1.38 (s, 9H), 1.23 (m, 1H). MS (ESI+) m/z 526.8 (M+H)+.

Provenance & Evidence