Cesium carbonate → HCID 86603661, compound

HRID 226352Notes

Reaction equation

HRID 226352 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21]([N:28]1[CH2:32][CH2:31][C@@H:30]([NH2:33])[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH4+].[Cl-]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:21]([N:28]1[CH2:32][CH2:31][C@@H:30]([NH:33][C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=2)[CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 688115Ethyl trans-4-BromocinnamateHCID 1519354(3R)-1-benzylpyrrolidin-3-amine

Product 1

HCID 86603661HCID 86603661, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl (2E)-3-(4-bromophenyl)acrylate (1.0 g) in dioxane (70 mL) was added palladium(II) acetate (88 mg), 2′-(dicyclohexylphosphino)-N,N-dimethyl-2-diphenylamine (231 mg), cesium carbonate (1.79 g), and (3R)-1-benzyl-3-pyrrolidinamine (760 mg). The mixture was heated at 90° C. for 24 hours. The resulting mixture was poured into sat NH4Cl aq solution and extracted with AcOEt. The organic layer was washed with sat. NH4Cl aq solution, water, and brine, and dried over Na2SO4. The solvent was removed in vacuo and residual brown oil was purified by silica gel column chromatography eluted with chloroform:methanol=9:1 to give ethyl (2E)-3-(4-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}phenyl)acrylate (1.017 g) as pale yellow oil.

Workup

  1. additionThe resulting mixture was poured
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with sat. NH4Cl aq solution, water, and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo and residual brown oil
  6. customwas purified by silica gel column chromatography
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-703a2e7bc21046fbb7d881d34af7b1c5
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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