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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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4-[(R)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-nitromethyl-butyryl]-2-methyl-benzoic acid tert-butyl ester → 4-[(R)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzoic acid tert-butyl ester

HRID 589632
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HRID 589632 반응식
[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C@@:15]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)([CH2:20][N+:21]([O-])=O)[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Ni].O>[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][C@:15]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)([C:16]([F:19])([F:18])[F:17])[CH2:20][N:21]=2)=[CH:9][C:8]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 1

HCID 547615654-[(R)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-nitromethyl-butyryl]-2-methyl-benzoic acid tert-butyl ester

생성물 1

HCID 547617404-[(R)-4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-benzoic acid tert-butyl ester수율 85.9%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 702Ethanol용매
HCID 962
Water
용매

실험 절차

Alternatively, the title compound can be obtained by carrying out the following experiment: To a vigorously stirred solution of 4-[(R)-3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-nitromethyl-butyryl]-2-methyl-benzoic acid tert-butyl ester (100 mg) in ethanol (6 mL) was added Raney Nickel (1.44 g, 50% suspension in water, previously washed with dry ethanol) and the reaction was stirred at room temperature under hydrogen (1 atm) for one hour. Then the solution was filtered over celite, and the resulting filtrate was concentrated in vacuo to give the title compound (78 mg) as a pale yellow solid. Chiral HPLC analysis (Chiralpack IA, Heptane:2-propanol:diethylamine=90:10:0.1, 1 ml/min, retention time 5.77 minutes (91.43%), 8.71 minutes (3.79%).

후처리

  1. washpreviously washed with dry ethanol) and the reaction
  2. filtrationThen the solution was filtered over celite
  3. concentrationthe resulting filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-860e77aeb5b9429ca4115054d914da32
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233920B2

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