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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
ノート
印刷プレビュー

反応式

HRID 394543 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 702Ethanol溶媒HCID 14923Ammonium Hydroxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7ba802a933334aa6aab0694fa4acc618
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06602886B2

反応ノート

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