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(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone → (2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanone

HRID 517379
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HRID 517379 반응식
[CH2:1]([Si:3]([CH2:35][CH3:36])([CH2:33][CH3:34])[O:4][C@H:5](/[CH:18]=[CH:19]/[Sn](CCCC)(CCCC)CCCC)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH3:2].C([Li])CCC.[Cu](C#N)C#N.C[Li].[CH2:49]([C:52]1[C:53](=[O:65])[CH2:54][C@@H:55]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH:56]=1)[CH:50]=[CH2:51].[NH4+].[Cl-].[NH4+].[OH-]>O1CCCC1>[CH2:49]([C@@H:52]1[C@@H:56](/[CH:19]=[CH:18]/[C@@H:5]([O:4][Si:3]([CH2:35][CH3:36])([CH2:1][CH3:2])[CH2:33][CH3:34])[CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C@H:55]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:59])[CH3:60])[CH2:54][C:53]1=[O:65])[CH:50]=[CH2:51]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 14189023(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enoneHCID 21863491Ammonium chloride ammonium hydroxideHCID 67428430(R,E)-triethyl(4-(tributylstannyl)-1-(3-(trifluoromethyl)phenoxy)but-3-en-2-yloxy)silaneHCID 178418260HCID 178418260, 화합물HCID 178418339ButyllithiumHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 131733344(2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanone수율 37.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A 100 ml three-necked flask was flame dried and allowed to be cooled under nitrogen. (R,E)-triethyl(4-(tributylstannyl)-1-(3-(trifluoromethyl)phenoxy)but-3-en-2-yloxy)silane (15.11 g, 23.8 mmol) and 20 ml tetrahydrofuran were added to the reaction flask, followed by dropwise addition of n-butyl lithium (14.9 ml, 1.6 M in hexane) at −70° C. A suspension solution of copper cyanide (2.13 g, 23.8 mmol) in 20 ml tetrahydrofuran was cooled to −20° C., followed by dropwise addition of methyl lithium (11.9 ml, 2 M in ether). The homogenous organo-metallic solution was cooled and added into the reaction flask while stirring for 60 minutes. Then, a solution of (R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone (3 g, 11.9 mmol) in 20 ml tetrahydrofuran at −70° C. was added to the reaction mixture for 10 minutes. After being stirred for another 20 minutes, the reaction mixture was poured into a mixture of 9/1 (v/v) saturated aqueous NH4Cl/NH4OH solution to be phase separated. The aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography and then concentrated under reduced pressure to provide 2.68 g of the title compound (37.7% yield).

후처리

  1. temperatureA 100 ml three-necked flask was flame
  2. customdried
  3. temperatureto be cooled under nitrogen
  4. additionadded into the reaction flask
  5. stirringAfter being stirred for another 20 minutes
  6. customseparated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe solid was filtered off
  10. customorganic solvent was evaporated off under vacuum
  11. customThe crude product was purified by chromatography
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b462cf8886a34f55834ff7be2617ada9
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115109B2

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