Water → HCID 58124047, compound

HRID 536675Notes

Reaction equation

HRID 536675 reaction equation
C[C:2]1([CH3:10])CCCC(C)(C)N1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:40][C@:41]12[C@H:55]([CH3:56])[C@H:45]([N:46]([C:49](=[O:54])[C:50]([F:53])([F:52])[F:51])[CH2:47][CH2:48]1)[CH2:44][C:43]1[CH:57]=[CH:58]C(OS(C(F)(F)F)(=O)=O)=[CH:60][C:42]2=1.CN(C)[CH:71]=[O:72].[OH2:74]>CC([O-])=O.CC([O-])=O.[Pd+2].CO>[CH3:71][O:72][C:2]([C:10]1[CH:58]=[CH:57][C:43]2[CH2:44][C@@H:45]3[C@@H:55]([CH3:56])[C@:41]([CH3:40])([C:42]=2[CH:60]=1)[CH2:48][CH2:47][N:46]3[C:49](=[O:54])[C:50]([F:53])([F:52])[F:51])=[O:74]

Participants

8

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 58123907HCID 58123907, compound

Product 1

HCID 58124047HCID 58124047, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

2,2,6,6-Tetramethylpiperidine (5.4 mL), 1,3-bis(diphenylphosphino)propane (1.30 g), and Pd(OAc)2 (0.78 g) are added in turn to a flask charged with trifluoromethanesulfonic acid (2R,6R,11S)-6,11-dimethyl-3-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl ester (7.0 g), dimethylformamide (30 mL), and methanol (30 mL) in argon atmosphere. The reaction flask is put under CO pressure (7 bar) and shaken at 70° C. for 17 h. After cooling to ambient temperature, water is added and the resulting mixture is extracted with Et2O. The combined organic extracts are washed with water and brine and dried (MgSO4). The solvent is evaporated to give the title compound as an oil that crystallizes while standing.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting mixture is extracted with Et2O
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-f2bc109c9dda4126bc672bb9501182a2
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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