1-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline → 1-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

HRID 599349노트

반응식

HRID 599349 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:13][CH:12]3[N:14]([C:15]([N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][CH2:19][CH2:18]4)=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH:8]=2)[CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:13][CH:12]3[N:14]([C:15]([N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][CH2:19][CH2:18]4)=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH:2]=1

참가 물질

4

반응물 1

HCID 248046411-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 249575581-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline수율 60.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
25 °C

실험 절차

In a high-pressure reactor, under nitrogen, 0.148 g of 5% palladium-on-charcoal is added to 0.240 g of 1-[(3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline solubilized in 9 ml of ethanol. The reaction mixture is placed under a hydrogen pressure of 3 atmospheres, at 25° C., and mechanically stirred for 15 hours. The palladium is filtered off on Whatman paper and washed with methanol. The solvent is evaporated off, and the residue then chromatographed on silica gel with an eluent gradient of heptane/ethyl acetate (3/7) to heptane/ethyl acetate (2/8). 0.146 g of 1-[(3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline is obtained.

후처리

  1. filtrationThe palladium is filtered off on Whatman paper
  2. washwashed with methanol
  3. customThe solvent is evaporated off
  4. customthe residue then chromatographed on silica gel with an eluent gradient of heptane/ethyl acetate (3/7) to heptane/ethyl acetate (2/8)

출처 및 근거

ORD 기록
ord-39ab8fd4fca14bb9ab6afb54b16e7abe
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897773B2

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