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

HRID 1856772노트

반응식

HRID 1856772 반응식
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]

참가 물질

5

반응물 4

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb619cae5f0a4c1da9253b0ead3507c2
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06143767

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