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 1501812Notes

Reaction equation

HRID 1501812 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cb19f948f7e4416ca38569a658209e73
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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