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

HRID 1856772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856772
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]

Komponenten

5

Edukt 4

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

Produkt 1

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

Versuchsvorschrift

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 (x3). 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.

Aufarbeitung

  1. temperatureice-cooled
  2. stirringAfter stirring at room temperature overnight
  3. extractionthe mixture was extracted with AcOEt (x3)
  4. washThe combined AcOEt extracts were washed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb619cae5f0a4c1da9253b0ead3507c2
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143767

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