Triethylamine → (R)-1-Acryloyl-pyrrolidine-2-carboxylic acid tert-butyl ester

HRID 1385779Notes

Reaction equation

HRID 1385779 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH:21]=[CH2:22]>ClCCl>[C:1]([O:5][C:6]([C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:20](=[O:23])[CH:21]=[CH2:22])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 6931635H-D-Pro-otbu

Product 1

HCID 54536265(R)-1-Acryloyl-pyrrolidine-2-carboxylic acid tert-butyl esterYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.0 g (29.2 mmol) D-Proline tert-butyl ester and 4.5 ml (32.1 mmol) triethylamine in 180 ml dichloromethane at 0 C. was added dropwise 3.6 ml (43.8 mmol) acryloyl chloride and stirring continued for 48 h at room temperature. The reaction mixture was then washed sequentially with water, saturated ammonium chloride solution, once more with water and then with saturated brine, and the aqueous phases back-extracted with dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated in vacuo to afford 6.6 g (100%) of the title compound as a yellow oil. MS m/e (%): 243 (M+NH4+, 33), 226 (M+H+, 100).

Workup

  1. washThe reaction mixture was then washed sequentially with water, saturated ammonium chloride solution, once more with water
  2. extractionwith saturated brine, and the 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-4ebd762a3c6946aba109d5716ec6b694
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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