[C:1]1([C@@H:7]([N:9]2[C@@H:14]([C:15](O)=[O:16])[C@H:13]3[CH2:18][C@@H:10]2[CH2:11][CH2:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.[NH2:31][OH:32].C(N(CC)CC)C>ClCCl.O1CCCC1.O>[OH:32][NH:31][C:15]([C@H:14]1[C@H:13]2[CH2:18][C@H:10]([CH2:11][CH2:12]2)[N:9]1[C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])=[O:16]To a solution of (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (224 mg, 0.913 mmol) in dichloromethane (3.5 ml) were added oxalyl chloride (0.17 ml, 1.92 mmol) and N,N-dimethylformamide (0.07 ml, 0.913 mmol) while being cooled with ice, and the mixture was stirred at room temperature for 30 minutes. Separately, to a suspension of hydroxylamine hydrochloride (254 mg, 3.65 mmol) in tetrahydrofuran (1.0 ml)-water (0.2 ml) was added triethylamine (0.78 ml, 5.57 mmol) at 0° C., and the mixture was stirred at 0° C. for 15 minutes. To this reaction mixture was added the acid chloride solution at 0° C., and the mixture was stirred at room temperature for 14 hours. The reaction mixture, with water added thereto, was extracted with chloroform. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (1% methanol/chloroform), to give the entitled compound (126 mg, 53%).
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