[CH3:1][C:2]1([CH2:8][OH:9])[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[C:10](ON1C(=O)CCC1=O)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].O.[OH-].[Na+]>CC#N.CC(N(C)C)=O.O.CC(N(C)C)=O.[Cl-].[Na+].O>[OH:9][CH2:8][C:2]1([CH3:1])[NH:3][CH2:4][CH2:5][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:7]1To crude (2-methylpiperazin-2-yl)methanol (10 C) (0.042 mol) dissolved in CH3CN/DMA/H2O (20 mL, 20 mL, 20 mL) cooled to 0° C. was added CBZ-OSu (9.5 g, 0.038 mol) in DMA (15 mL). The reaction was stirred at 0° C. for 30 min then warmed to RT. To the mixture was added H2O (500 mL), sat'd brine (50 mL) and 1M NaOH (50 mL), then the residue was extracted four times with EtOAc (100 mL). The combined EtOAc layers were washed twice with brine then dried over MgSO4 and the solvent removed in vacuo to give racemic benzyl 3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate (9.7 g). HPLC RT: 1.302 min (4 min Chromolith column TFA).
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