Potassium Carbonate → tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate

HRID 2376094Notes

Reaction equation

HRID 2376094 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[N:6][CH:7]=1.[NH2:14][C@@H:15]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)N(C)CC1>[CH3:13][O:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]1[N:6]=[CH:7][C:2]([NH:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 86603715HCID 86603715, compound

Product 1

HCID 67128781tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylateYield 69.9%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (680 mg) in DMI (1.4 mL) was added tert-butyl (3R)-3-amino-1-pyrrolidinecarboxylate (957 mg) and K2CO3 (1.42 g), which was stirred at 120° C. for 2 hours. The reaction mixture was filtered and evaporated in vacuo. To the residue was added H2O, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl (3R)-3-({5-[(1E)-3-methoxy-3-oxo-1-propen-1-yl]-2-pyrazinyl}amino)-1-pyrrolidinecarboxylate (834 mg) as a off-white powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. additionTo the residue was added H2O, which
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2d2a9c86a69746a4a69d1736afee8fde
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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