[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.[NH4+:18].[OH-]>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH2:18])=[O:11]
A solution of 2-(bicyclo[2.2.1]heptan-2-yl)acetic acid (0.50 g, 3.24 mmol) in DCM (30 mL) was treated with oxalyl chloride (0.426 mL, 4.86 mmol), followed by a catalytic amount of DMF (1 drop) and stirred at RT for 2 h. A solution of NH4OH (˜15M, 2 mL, ˜30 mmol) in THF (5 mL) was added drop wise and the mixture stirred at RT overnight. The mixture was concentrated to dryness and the residue was dissolved in EtOAc, washed with brine, dried over MgSO4 and concentrated to dryness to afford 2-(bicyclo[2.2.1]heptan-2-yl)acetamide (480 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.19 (s, 1H), 6.65 (s, 1H), 2.14 (s, 1H), 1.91 (m, 3H), 1.75 (m, 1H), 1.35 (m, 4H), 1.11 (m, 4H); MS (ESI) m/z: 154.2 (M+H+).
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