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4-Cyano-4-(3,4-dichlorophenyl)-7-(tetrahydropyran-4-yloxy)-heptanoic Acid Ethyl Ester → 5-(3,4-Dichlorophenyl)-5-[3-(tetrahydropyran-4-yloxy)-propyl]-2-piperidone

HRID 394543
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HRID 394543 반응식
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]([C:26]#[N:27])([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH2:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)C>CCO.[NH4+].[OH-].[Ni]>[Cl:25][C:20]1[CH:19]=[C:18]([C:7]2([CH2:8][CH2:9][CH2:10][O:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[CH2:26][NH:27][C:4](=[O:3])[CH2:5][CH2:6]2)[CH:23]=[CH:22][C:21]=1[Cl:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 1

HCID 158876524-Cyano-4-(3,4-dichlorophenyl)-7-(tetrahydropyran-4-yloxy)-heptanoic Acid Ethyl Ester

생성물 1

HCID 158876535-(3,4-Dichlorophenyl)-5-[3-(tetrahydropyran-4-yloxy)-propyl]-2-piperidone수율 84.8%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 702Ethanol용매HCID 14923Ammonium Hydroxide용매

실험 절차

Raney Ni is added to a solution of cyanoester (5) (8.5 g, 19.84 mmol) in absolute EtOH (200 mL) and concentrated NH4OH (40 mL). The mixture was subjected to a H2 (51.8 psi) Par for 64.5 hours. The reaction mixture was filtered through celite, and N2 gas was passed through the solution to remove NH3. EtOH was then evaporated, and water is azeotropically removed with toluene. The crude oil is purified by flash chromatography (Ch2Cl2-MeOH/95:5) to give a colorless solid (6.5 g, 84.8% yield), mp ˜45° C.

후처리

  1. filtrationThe reaction mixture was filtered through celite, and N2 gas
  2. customto remove NH3
  3. customEtOH was then evaporated
  4. customwater is azeotropically removed with toluene
  5. customThe crude oil is purified by flash chromatography (Ch2Cl2-MeOH/95:5)

출처 및 근거

ORD 기록
ord-7ba802a933334aa6aab0694fa4acc618
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06602886B2

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