Thiomorpholine → 2-[(1S)-6-(4-Thiomorpholinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol

HRID 2056778노트

반응식

HRID 2056778 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.ClCCl.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]>[N:15]1([C:2]2[CH:3]=[CH:4][C:5]3[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=3[CH:14]=2)[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1

참가 물질

8

반응물 4

HCID 67164ThiomorpholineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

생성물 1

HCID 693083652-[(1S)-6-(4-Thiomorpholinyl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.26 g, 0.99 mmol) was dissolved in dry toluene (10 mL) and degassed. Thiomorpholine (0.14 mL, 1.48 mmol), tris(dibenzylideneacetone)dipalladium (51 mg), (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (77 mg) and sodium tert-butoxide (0.126 g, 1.3 mmol) were added and the mixture heated under reflux with stirring, under a nitrogen atmosphere, for 24 h. The reaction was cooled to room temperature, diluted with dichloromethane, filtered through celite and washed with water. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, to yield the title compound.

후처리

  1. customdegassed
  2. temperaturethe mixture heated
  3. temperatureunder reflux
  4. filtrationfiltered through celite
  5. washwashed with water
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-76afd44a0f904b60a5419ac3aac33177
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

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