Triethylamine → (R)-1-acryloyl-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1385718Notes

Reaction equation

HRID 1385718 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>ClCCl>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:24](=[O:27])[CH:25]=[CH2:26])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 53983923(R)-1-acryloyl-pyrrolidine-2-carboxylic acid benzyl esterYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 390 mg (1.6 mmol) D-Proline benzyl ester hydrochloride and 0.47 ml (3.4 mmol) triethylamine in 20 ml dichloromethane at 0° C. was added dropwise 0.2 ml (2.4 mmol) acryloyl chloride and stirring continued for 24 h at room temperature. The reaction mixture was then washed sequentially with water, 1M hydrochloric acid and once more with water, and the aqueous phases back-extracted with dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated in vacuo to afford 420 mg (100%) of the title compound (R)-1-acryloyl-pyrrolidine-2-carboxylic acid benzyl ester as a colorless oil.

Workup

  1. washThe reaction mixture was then washed sequentially with water, 1M hydrochloric acid and once more with water
  2. extractionthe aqueous phases back-extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b14d26f6a7e4585b62205775eefa93a
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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