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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Formic Acid → (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

HRID 407858
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인쇄 미리보기

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HRID 407858 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.N1CCCCC1.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[C:17]=1[CH:24]1[C:32](=[O:33])[CH:31]2[CH:26]([CH:27]3[O:34][CH:30]2[CH:29]=[CH:28]3)[C:25]1=[O:35].C(O)=O>CN(C)C=O.ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([CH:29]2[CH2:28][CH:27]3[O:34][CH:30]2[CH:31]2[CH:26]3[C:25](=[O:35])[CH:24]([C:17]3[C:18]([CH3:23])=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=3[CH3:15])[C:32]2=[O:33])[CH:5]=[CH:6][CH:7]=1
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참가 물질

8

반응물 4

HCID 284Formic AcidHCID 8082PiperidineHCID 707251-Fluoro-3-iodobenzeneHCID 67283862(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

생성물 1

HCID 67284052(1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

Bis(triphenylphosphine)palladium diacetate (20 mg, 0.024 mmol), 1-fluoro-3-iodo-benzene (104 mg, 0.47 mmol) and piperidine (0.16 ml, 1.6 mmol) are added to a solution of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (0.20 g, 0.71 mmol) in dry N,N-dimethylformamide (2 ml). Formic acid (0.06 ml, 1.6 mmol) is added and the reaction mixture is heated at 50° C. for 2 hours. The reaction mixture is cooled to room temperature, water (1 ml) and dichloromethane (1 ml) are added, and the mixture is stirred for 1 hour. The two phases are separated, the organic phase collected and the solvent is evaporated. The residue is purified by preparative reverse-phase HPLC to give (1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customThe two phases are separated
  3. customthe organic phase collected
  4. customthe solvent is evaporated
  5. customThe residue is purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-4394443872004514b123596c6f130ee9
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754242B2

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