[CH2:1]([N:5]1[CH2:9][C@H:8]2[CH2:10][C:11](=O)[CH2:12][C@H:7]2[CH2:6]1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]([N:5]1[CH2:9][C@H:8]2[CH2:10][C:11](=[N:15][OH:16])[CH2:12][C@H:7]2[CH2:6]1)[CH2:2][CH2:3][CH3:4]A suspension of (3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one (0.467 g, 2.58 mmol), hydroxylamine hydrochloride (0.430 g, 6.19 mmol) and sodium acetate (0.842 g, 6.19 mmol) in ethanol (21 ml) and water (7 ml) is heated to reflux for 1 hour. The ethanol is evaporated and the residue partitioned between saturated aqueous NaHCO3 and EtOAc. The organic phase is washed with brine, dried (MgSO4) and evaporated to afford (3aS,6aR)-2-butylhexahydrocyclopenta[c]pyrrol-5-one oxime, MH+197.
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