tert-Butanol → (2S,3S)-1-tert-Butoxycarbonyl-3-(2-methoxybenzyl)amino-2-phenylpiperidine
Reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C@H:7]1[CH2:12][CH2:11][CH2:10][NH:9][C@H:8]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].O(OC(C(C)(C)C)=O)[O:26][C:27](C(C)(C)C)=O.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[C:40]([O:44][C:27]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:7]([NH:6][CH2:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=2[O:2][CH3:1])[C@@H:8]1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:26])([CH3:43])([CH3:42])[CH3:41]Participants
5
Procedure
To a stirred and ice-cooled mixture of Compound 15 (10 g, 27 mmol), 3M NaOH aq. (36 ml, 110 mmol) and tert-BuOH (15 ml) was added (tert-BuOCO)2O (7.4 g, 34 mmol) in one portion. After stirring at room temperature overnight, the mixture was extracted with AcOEt. The combined AcOEt extracts were washed with H2O, and sat. NaCl aq, dried (Na2 SO4), and concentrated in vacuo to give Compound 16 (11 g, quant.) as a pale yellow oil.