Br.C(OC([N:12]1[C@H:17]([CH3:18])[CH2:16][N:15]([CH2:19][C:20]2[CH:29]=[C:28]3[C:23]([C:24]([Cl:30])=[CH:25][CH:26]=[N:27]3)=[CH:22][CH:21]=2)[C:14](=[O:31])[C@@H:13]1[CH3:32])=O)C1C=CC=CC=1.C(N(CC)CC)C>C(O)(=O)C.C(OCC)(=O)C>[Cl:30][C:24]1[C:23]2[C:28](=[CH:29][C:20]([CH2:19][N:15]3[CH2:16][C@@H:17]([CH3:18])[NH:12][C@@H:13]([CH3:32])[C:14]3=[O:31])=[CH:21][CH:22]=2)[N:27]=[CH:26][CH:25]=1
A 33% solution of hydrogen bromide in acetic acid (10 mL) is added to (2S,6R)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (1.04 g, 2.38 mmol). The reaction is left to stir at room temperature for one hour. The reaction mixture is diluted with ethyl acetate and stirred vigorously to force the product to precipitate out of solution. The ethyl acetate is decanted off and the precipitate is purified on a silica gel column (1% triethylamine/3% methanol/methylene chloride) to 582 mg (81% yield) of (3S,5R)-1-(4-chloro-quinolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one as a white solid.
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