Water → HCID 178471530, compound

HRID 1713869Notes

Reaction equation

HRID 1713869 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.FC(F)(F)S(O[C:27]1[CH:32]=[CH:31][C:30]([C@H:33]2[CH2:38][CH2:37][C@H:36]([CH:39]([CH3:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1)(=O)=O.O>C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:8]1([C:7](=[N:20][C:27]2[CH:32]=[CH:31][C:30]([C@H:33]3[CH2:34][CH2:35][C@H:36]([CH:39]([CH3:45])[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:37][CH2:38]3)=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 178471539HCID 178471539, compound

Product 1

HCID 178471530HCID 178471530, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Caesium carbonate (4.0 g, 12.4 mmol), R-BINAP (330 mg, 0.53 mmol), palladium acetate (119 mg, 0.53 mmol) and benzophenone imine (2.2 mL, 13.2 mmol) were added sequentially, each in one portion, to a stirred solution of trans-ethyl 2-[4-(4-{[(trifluoromethyl)-sulfonyl]oxy}phenyl)cyclohexyl]propanoate in THF (50 mL) and the reaction mixture was heated at 65° C. for 70 h under an argon atmosphere. The reaction mixture was cooled to room temperature and concentrated in vacuo to leave a residue. The residue was taken up in EtOAc (75 mL) and H2O (25 mL) was added. The layers were separated and the organic layer was extracted with brine (25 mL), dried and concentrated in vacuo to leave a residue. The residue was purified by chromatography, eluting with 10-50% EtOAc in isohexane, to give the title compound (2.3 g, 59%) as an oil; 1H NMR δ (CDCl3) 1.07-1.25 (2H, m), 1.15 (3H, d), 1.3 (3H, t), 1.35-1.5 (2H, m), 1.55-1.7 (2H, m), 1.72-1.8 (1H, m), 1.83-1.95 (2H, m), 2.24-2.43 (2H, m), 4.15 (2H, q), 6.7 (2H, d), 7.0 (2H, d), 7.15 (2H, d), 7.23-7.35 (1H, m), 7.4 (2H, dd), 7.47-7.55 (2H, m), 7.78 (2H, d), 7.84 (1H, d); MS m/e MH+ 440.

Workup

  1. concentrationconcentrated in vacuo
  2. customto leave a residue
  3. customThe layers were separated
  4. extractionthe organic layer was extracted with brine (25 mL)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto leave a residue
  8. customThe residue was purified by chromatography
  9. washeluting with 10-50% EtOAc in isohexane

Sources & evidence

ORD record
ord-b70b59adf28842538ab709797f445e11
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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