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1-Chloro-2,2-difluoro-1-phenyl-1,3,6,7,9,10-hexahydro-2H-8-aza-cyclohepta[e]indene-8-carboxylic acid ethyl ester → 2,2-Difluoro-1-phenyl-1,3,6,7,9,10-hexahydro-2H-8-aza-cyclohepta[e]indene-8-carboxylic acid ethyl ester

HRID 925207
ノート
印刷プレビュー

反応式

HRID 925207 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[C:12](Cl)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[CH:12]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]
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 2

HCID 867253171-Chloro-2,2-difluoro-1-phenyl-1,3,6,7,9,10-hexahydro-2H-8-aza-cyclohepta[e]indene-8-carboxylic acid ethyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 867253192,2-Difluoro-1-phenyl-1,3,6,7,9,10-hexahydro-2H-8-aza-cyclohepta[e]indene-8-carboxylic acid ethyl ester収率 78.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702
Ethanol
溶媒

実験手順

Into a 500 ml Parr bottle, the product from step (d) (5.9 g, 14.56 mmol) dissolved in EtOH (150 ml) was added. To the solution, 5% Pd—C (3 g) was added. The reaction mixture was shaken over hydrogen (50 psi) for 16 hours. The reaction mixture was filtered through celite and the volatiles were evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes) gave the sub-title compound as a colorless oil (4.25 g). 1H NMR (300 MHz, CHCl3) δ 7.28-7.26 (m, 3H); 7.10 (s, 2H); 7.01-6.98 (m, 2H); 4.64 (d, J=20.1 Hz, 1H); 4.11-4.01 (m, 2H); 3.66-3.60 (m, 1H); 3.54-3.31 (m, 4H); 3.13-3.06 (m, 1H); 2.89-2.85 (m, 2H); 2.67-2.47 (m, 2H); 1.26-1.22 (m, 3H); MS: ESI (positive): 372 (M+1).

後処理

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe volatiles were evaporated in vacuo
  4. customto give the crude product
  5. customPurification
  6. washby silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-579d6055a26641b6a313aa55a7b8bd9c
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284277B2

反応ノート

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