Benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate → 2-(Pyrrolidin-2-yl)benzo[d]oxazole-7-carboxamide

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Reaction Steps

A mixture of benzyl 2-(7-carbamoylbenzo[d]oxazol-2-yl)pyrrolidine-1-carboxylate (68 mg, 0.19 mmol), 10% Pd/C (20 mg) in methanol (30 ml) was stirred at room temperature over 1 atm hydrogen for 2 hr. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by pre-HPLC to give 6 mg of 2-(pyrrolidin-2-yl)benzo[d]oxazole-7-carboxamide. Yield 13%. LC-MS (ESI) m/z: 232 (M+1)+. 1H-NMR (400 MHz, CDCl3): δ 1.24 (brs, 1H), 1.97 (m, 2H), 2.21 (m, 1H), 2.35 (m, 1H), 3.12 (m, 1H), 3.22 (m, 1H), 4.58 (m, 1H), 5.99 (brs, 1H), 7.03 (brs, 1H), 7.43-7.47 (t, J=8 Hz, 1H), 7.85-7.87 (d, J=8 Hz 1H), 8.08-8.09 (d, J=7.6 Hz, 1H).

Provenance & Evidence