Hydrochloric Acid → (S)-benzyl 3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride
Reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O.[ClH:26]>C(#N)C>[ClH:26].[OH:1][CH2:2][C@H:3]1[NH:4][CH2:5][CH2:6][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8]1Participants
4
Procedure
4-Benzyl 1-tert-butyl (2S)-2-(hydroxymethyl)piperazine-1,4-dicarboxylate (see WO 02/000631; 1.6 g, 4.6 mmol was dissolved in acetonitrile (25 mL) and to the resultant solution was added concentrated HCl (1 mL). The mixture was stirred at RT overnight and then the solvent was removed by evaporation. There was obtained 1.3 g (100%) of benzyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate hydrochloride as a colorless oil. 1H NMR (500 MHz, CD3OD): 3.1-3.4 (m, 5H), 3.7 (m, 1H), 3.8 (m, 1H), 4.2 (m, 2H), 5.2 (m, 2H), 7.2-7.4 (m, 5H); LCMS: m/z 251 (M+1)+.