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Potassium Phosphate, Tribasic → Tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501812
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HRID 1501812 반응식
Br[C:2]1[C:6](=[O:7])[O:5][CH2:4][C:3]=1[N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[C:9]1=[O:25].[B-](F)(F)(F)[CH:27]=[CH2:28].[K+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:25]=[C:9]1[C:10]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:11][CH2:12][N:8]1[C:3]1[CH2:4][O:5][C:6](=[O:7])[C:2]=1[CH:27]=[CH2:28]
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참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 23679353Potassium vinyltrifluoroborateHCID 86709468tert-Butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

생성물 1

HCID 86709509Tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

tert-butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (2.2 g, 5.30 mmol), potassium trifluoro(vinyl)borate (1.06 g, 7.95 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.345 g, 0.530 mmol) and potassium phosphate tribasic (10.60 mL, 10.60 mmol) were taken up in THF (44.1 mL) in a sealed tube, de-gassed and the resulting mixture was heated overnight at 70° C. The reaction mixture was cooled to room temperature and then was diluted with EtOAc and water. After separation of layers, the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried over anhydrous MgSO4, filtered, concentrated and purified by silica gel column chromatography using (30-100) % EtOAc/hexanes as mobile phase to provide the title compound.

후처리

  1. customde-gassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionwas diluted with EtOAc and water
  4. customAfter separation of layers
  5. extractionthe aqueous layer was extracted with EtOAc (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cb19f948f7e4416ca38569a658209e73
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206198B2

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