tert-Butanol → (2S,3S)-1-tert-Butoxycarbonyl-3-(2-methoxybenzyl)amino-2-phenylpiperidine

HRID 481496Notes

Reaction equation

HRID 481496 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

Reactant 4

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 5311057CP-99994HCID 14215521(tBuOCO)2O

Product 1

HCID 11223212(2S,3S)-1-tert-Butoxycarbonyl-3-(2-methoxybenzyl)amino-2-phenylpiperidine

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.

Workup

  1. temperatureice-cooled
  2. stirringAfter stirring at room temperature overnight
  3. extractionthe mixture was extracted with AcOEt
  4. washThe combined AcOEt extracts were washed with H2O, and sat. NaCl aq
  5. customdried (Na2 SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dce5cd10aea4d989a7ec092cd80e30a
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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