Triethylamine → 1-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

HRID 1511546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511546
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:11]([O:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]1)=[O:12])[CH2:6]2.[CH:30]([B-](F)(F)F)=[CH2:31].[K+].C(N(CC)CC)C>C(O)C.OS([O-])(=O)=O.[K+]>[CH:30]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:11]([O:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]1)=[O:12])[CH2:6]2)=[CH2:31]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 534655661-(1,1-Dimethylethyl) 2-methyl (2S,4R)-4-(((4-bromo-1,3-dihydro-2H-isoindol-2-yl)carbonyl)oxy)-1,2-pyrrolidinedicarboxylate

Produkt 1

HCID 453783721-t-Butyl 2-methyl (2S,4R)-4-{[(4-vinyl-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516920Potassium bisulfateLösungsmittel

Versuchsvorschrift

To a solution of 1-t-butyl 2-methyl (2S,4R)-4-{[(4-bromo-1,3-dihydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboxylate (10.0 g, 21.3 mmol) in ethanol (200 mL) was added potassium vinyltrifluoroborate (4.28 g, 32 mmol) and triethylamine (4.5 mL, 32 mmol) followed by dichloro[1,1-bis(diphenylphosphino)ferrocene]palladium (II) chloride dichloromethane adduct (175 mg, 0.21 mmol). The reaction mixture was heated to reflux for 6 h, cooled to room temperature, diluted with 10% aqueous KHSO4 and the ethanol removed by evaporation in vacuo. The aqueous residue was extracted with EtOAc and the organic phase washed with brine, dried over Na2SO4, solvent evaporated and crude product purified by chromatography on silica eluting with 40-60% EtOAc/hexane to give, after evaporation, the title compound (8.18 g). LRMS (ESI) m/z 417.2 [(M+H)+; calcd for C22H29N2O6: 417.2].

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customthe ethanol removed by evaporation in vacuo
  4. extractionThe aqueous residue was extracted with EtOAc
  5. washthe organic phase washed with brine
  6. dry with materialdried over Na2SO4, solvent
  7. customevaporated
  8. customcrude product purified by chromatography on silica eluting with 40-60% EtOAc/hexane
  9. customto give
  10. customafter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0533baff1fdc4b3b8694a428e5e6619b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216999B2

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