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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → (1R,2R,3S,5S)-3-Benzoyloxy-8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester

HRID 916351
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HRID 916351 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]([C@H:18]1[C@@H:25]([O:26][C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])[CH2:24][C@H:22]2[NH:23][C@@H:19]1[CH2:20][CH2:21]2)=[O:17].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:14][O:15][C:16]([C@H:18]1[C@@H:25]([O:26][C:27](=[O:28])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:24][C@H:22]2[N:23]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]([C:12]#[N:13])=[CH:4][CH:3]=3)[C@@H:19]1[CH2:20][CH2:21]2)=[O:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 644007(-)-NorcocaineHCID 146621114-Bromo-1-naphthonitrile

생성물 1

HCID 69227082(1R,2R,3S,5S)-3-Benzoyloxy-8-(4-cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester수율 29%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매

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온도
110 °C

실험 절차

Adapting a protocol by Wolfe and Buchwald (Tetrahedron Lett., 1997, 37, 6359-6362), 1-bromo-4-cyanonaphthalene (124 mg, 0.53 mmol, Cakmak O. et al., Collect. Czech. Chem. Commun. 2000, 65, 1791-1804), norcocaine (185 mg, 0.64 mmol), Pd2(dba)3 (23.8 mg, 0.026 mmol), rac-BINAP (24.7 mg, 0.040 mmol) and caesium carbonate (242 mg, 0.74 mmol) were placed in an argon flushed vial, toluene (1.0 mL) was added and the resulting mixture was stirred under argon atmosphere at 110° C. overnight. The crude was then concentrated in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 4× eluted) afforded the title compound (68 mg, 29%) as an oil.

후처리

  1. customet al., Collect
  2. concentrationThe crude was then concentrated in vacuo and purification by preparative TLC (ethyl acetate/n-heptane 1:4, 4× eluted)

출처 및 근거

ORD 기록
ord-da4d955b64a34452a654cc25c6250c4e
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07268232B2

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