1-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehyde → 1-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)-3,4-methylenedioxyphenethyl]piperidine

HRID 1837730노트

반응식

HRID 1837730 반응식
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[Br-].[CH3:19][S:20]([C:23]1[C:48]2[O:49][CH2:50][O:51][C:47]=2[CH:46]=[CH:45][C:24]=1[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:22])=[O:21].CC(C)([O-])C.[K+].[H][H]>CN(C)C=O.C(O)C.[C].[Pd].O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:25][C:24]3[CH:45]=[CH:46][C:47]4[O:51][CH2:50][O:49][C:48]=4[C:23]=3[S:20]([CH3:19])(=[O:22])=[O:21])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][N:4]=1

참가 물질

9

반응물 4

HCID 226784071-[(2-Methoxy-3-pyridinyl)methyl]-4-piperidinecarboxaldehydeHCID 22678528(2-(Methylsulfonyl)-3,4-methylenedioxybenzyl]triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 226784051-[(2-Methoxy-3-pyridyl)methyl]-4-[2-(methylsulfonyl)-3,4-methylenedioxyphenethyl]piperidine

시약·촉매·용매 4

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

800 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-piperidinecarboxaldehyde, 1.90 g of [2-(methylsulfonyl)-3,4-methylenedioxybenzyl]triphenylphosphonium bromide and 384 mg of potassium tert-butoxide were suspended in 10 ml of N,N-dimethylformamide, and the mixture was stirred for 1 hour at room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:4). The resulting product and 400 mg of 10% palladium-carbon powder (water-containing product) were suspended in 40 ml of ethanol. After replacing the atmosphere of a container with hydrogen, the mixture was stirred at room temperature under normal pressure for 30 minutes. The reaction solution was filtered, and the filtrate was evaporated, to give the title compound as a colorless oil (quantitatively).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by NH
  6. customform silica gel column chromatography (ethyl acetate:hexane=1:4)
  7. stirringthe mixture was stirred at room temperature under normal pressure for 30 minutes
  8. filtrationThe reaction solution was filtered
  9. customthe filtrate was evaporated

출처 및 근거

ORD 기록
ord-19636afcdf914e62b5cfa3629579131a
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784192B2

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