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 599349ノート

反応式

HRID 599349 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-39ab8fd4fca14bb9ab6afb54b16e7abe
出典データセット
uspto-grants-2011_03
特許番号
US07897773B2

反応ノート

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