Ethyl Acrylate → HCID 86603763, compound

HRID 226457Notes

Reaction equation

HRID 226457 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([C:21]2[CH:26]=[N:25][CH:24]=[C:23](Cl)[N:22]=2)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)C(C)C)(C)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20])[C:21]2[N:22]=[C:23](/[CH:30]=[CH:29]/[C:28]([O:32][CH2:33][CH3:34])=[O:31])[CH:24]=[N:25][CH:26]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 86603761HCID 86603761, compound

Product 1

HCID 86603763HCID 86603763, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of tert-butyl [(3R)-1-benzyl-3-pyrrolidinyl](6-chloro-2-pyrazinyl)carbamate (910 mg) in DMF (15 mL) was added ethyl acrylate (1.27 mL), palladium(II) acetate (26 mg), tris(2-methylphenyl)phosphine (107 mg), and N,N-diisopropylethylamine (1.22 mL). The mixture was stirred in the sealed tube at 150° C. for 3 days. The resulting mixture was allowed to cool to ambient temperature, poured into water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (96:4 v/v) to give ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl](tert-butoxycarbonyl)amino}-2-pyrazinyl)acrylate (755 mg) as a pale yellow foam.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of chloroform and methanol (96:4 v/v)

Sources & evidence

ORD record
ord-4156c8e867384e0d99bbe08bf55502f9
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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