Morpholine → HCID 68454907, compound

HRID 2358396Notes

Reaction equation

HRID 2358396 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([O:55][C:56](=[O:77])[CH:57]=[CH:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]([CH3:68])([CH3:67])[CH3:66])=[CH:61][C:60]=1OS(C(F)(F)F)(=O)=O)[CH3:54].[NH:78]1[CH2:83][CH2:82][O:81][CH2:80][CH2:79]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:53]([O:55][C:56](=[O:77])[CH:57]=[CH:58][C:59]1[CH:64]=[CH:63][C:62]([C:65]([CH3:68])([CH3:67])[CH3:66])=[CH:61][C:60]=1[N:78]1[CH2:83][CH2:82][O:81][CH2:80][CH2:79]1)[CH3:54]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 76587262HCID 76587262, compound

Product 1

HCID 68454907HCID 68454907, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

Palladium(II) acetate (1.4 mg, 0.006 mmole, 6 mol % eq), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (7.5 mg, 0.012 mmole, 12 mol % eq), and cesium carbonate (50.3 mg, 0.155 mmole, 1.5 eq) were added into anhydrous toluene. 3-(4-tert-Butyl-2-trifluoromethanesulfonyloxyphenyl)acrylic acid ethyl ester (36.2 mg, 0.103 mmol, 1 eq) in toluene solvent was added by cannula. Morpholine (13.5 μl, 0.155 mmol, 1.5 eq) was added. The mixture was stirred for 12 hr in reflux. After confirming the completion of the reaction with TLC, the reaction mixture was filtered with celite. The filterate was concentrated in vacuo, and then the residue was purified with column chromatography(n-Hx:EA=12:1) to give title product (16.7 mg, 51.2%).

Workup

  1. temperaturein reflux
  2. customthe completion of the reaction with TLC
  3. filtrationthe reaction mixture was filtered with celite
  4. concentrationThe filterate was concentrated in vacuo
  5. customthe residue was purified with column chromatography(n-Hx

Sources & evidence

ORD record
ord-cdc88a04e5a34f60b79507b4f36bc3ac
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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