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

HRID 1740734Notes

Reaction equation

HRID 1740734 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[CH2:7][NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].O(OC(C(C)(C)C)=O)[O:28][C:29](C(C)(C)C)=O.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:29]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][CH2:7][C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]=2[O:4][CH3:3])[C@@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:28])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 14215521(tBuOCO)2OHCID 68466923CP 99994 dihydrochloride

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 3 (10.0 g, 27.1 mmol), 3.0 M NaOH aq. (36.1 ml, 108.4 mmol) and tert-BuOH (15.0 ml) was added (tert-BuOCO)2O (Boc2O, 7.39 g, 33.8 mmol). After stirring at room temperature overnight, the mixture was extracted with AcOEt (×3). The combined AcOEt extracts were washed with sat. NaHCO3 and brine, dried over Na2SO4, and concentrated to give Compound 4 (11.3 g, quant.) as a pale yellow syrup.

Workup

  1. temperatureice-cooled
  2. stirringAfter stirring at room temperature overnight
  3. extractionthe mixture was extracted with AcOEt (×3)
  4. washThe combined AcOEt extracts were washed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d513e0561f44b60a8887f137a178c89
Source dataset
uspto-grants-1999_10
Patent number
US05972930

Reaction notes

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