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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
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HRID 925207 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 702
Ethanol
용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-579d6055a26641b6a313aa55a7b8bd9c
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284277B2

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