[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][NH:17][C@H:16]([CH3:20])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][N:17]([CH2:22][C:21]([O:25][CH3:26])=[O:24])[C@H:16]([CH3:20])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1
To a solution of (R)-1-(1-(4-chlorophenyl)cyclohexyl)-3-methylpiperazine (0.6 g, 2.05 mmol) in dichloromethane at room temperature were added methyl glyoxalate (0.23 g, 2.61 mmol), acetic acid (0.18 g, 3 mmol) and Na(OAc)3BH (1.08 g, 5.1 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. It was purified by silica gel (100-200 mesh) column chromatography eluting with ethyl acetate in n-hexanes to afford 0.49 g of (R)-methyl 2-(4-(1-(4-chlorophenyl)cyclohexyl)-2-methyl-piperazin-1-yl)acetate.
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