Cl[C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=1[C:9]1([CH2:18][CH3:19])[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17].Br.N>ClCCl.C(O)(=O)C>[CH2:18]([C:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:8])[CH:2]=2)[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17])[CH3:19]A solution of 3-(2-chloro-3-oxocyclohex-1-enyl)-3-ethyl-hexahydro-1-methylazepin-2-one (5.68 g) in dichloromethane (60 ml) was treated with 48% HBr in acetic acid (2 ml). After 12 hours the mixture was treated with excess aqueous ammonia, the organic solvent removed under reduced pressure and the resulting solid removed by filtration to give the title compound, m.p. 178°-80° C. (EtOAc).
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