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Ethyl Acetate → (S)-1-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}piperidine

HRID 743373
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HRID 743373 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:8]=[CH:9][CH:10]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([CH2:33]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(OCC)(=O)C>CC(N(C)C)=O.O>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([CH2:33][O:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=2)[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]
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참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenolHCID 45158786tert-Butyl (3S)-3-{[(4-methylbenzene-1-sulfonyl)oxy]methyl}piperidine-1-carboxylate

생성물 1

HCID 53797160(S)-1-t-Butoxycarbonyl-3-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}piperidine수율 96.5%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

0.295 g of a 50% w/w dispersion of sodium hydride in mineral oil was added to a solution of 1.55 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 21) in 60 ml of dimethylacetamide, whilst ice-cooling and stirring, and the mixture was stirred at the same temperature for 15 minutes. 2.50 g of (S)-1-t-butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine were then added to the mixture, whilst ice-cooling, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 6 hours. At the end of this time, 250 ml of ethyl acetate and 150 ml of water were added to the reaction mixture, and the ethyl acetate layer was separated. The aqueous layer was extracted with 50 ml of ethyl acetate once, and the ethyl acetate layer and the extract were combined, washed with a saturated aqueous solution of sodium chloride twice, dried over anhydrous magnesium sulfate and concentrated by distillation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.78 g (yield 96%) of the title compound as a colorless oil.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 15 minutes
  3. temperaturecooling
  4. stirringthe mixture was stirred at the same temperature for 30 minutes
  5. customthe ethyl acetate layer was separated
  6. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate once
  7. washwashed with a saturated aqueous solution of sodium chloride twice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated by distillation under reduced pressure
  10. customThe concentrate was purified by column chromatography through silica gel
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-eebb613ac410412794b1ee66b188c4da
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05556864

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