D-Proline → (2R)-1-Methacryloylpyrrolidin-2-carboxylic Acid

HRID 1249648Notes

Reaction equation

HRID 1249648 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[C:9](Cl)(=[O:13])[C:10]([CH3:12])=[CH2:11]>[OH-].[Na+].CCOCC>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 2

HCID 8988D-ProlineHCID 13528Methacryloyl chloride

Product 1

HCID 11615290(2R)-1-Methacryloylpyrrolidin-2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

D-Proline (50 g) was dissolved in 430 ml of 20% aqueous sodium hydroxide and the resultant solution was stirred with ice bath cooling as 217 ml ether was added followed by dropwise addition of 50 g of methacryloyl chloride in 400 ml ether over about 45 minutes. After another 30 minutes, the aqueous phase was removed and washed once with additional ether. The aqueous phase was then acidified with concentrated hydrochloric acid and extracted three times with ethyl acetate. These combined ethyl acetate extracts were evaporated in vacuo. The resultant residue was crystallized from a mixture of toluene and petroleum ether to yield the title compound, N-methacryloyl-D-proline, which was then recrystallized from acetone/petroleum ether to yield 51.5 g (53%) of purified material.

Workup

  1. additionwas added
  2. customthe aqueous phase was removed
  3. washwashed once with additional ether
  4. extractionextracted three times with ethyl acetate
  5. customThese combined ethyl acetate extracts were evaporated in vacuo
  6. customThe resultant residue was crystallized from a mixture of toluene and petroleum ether

Sources & evidence

ORD record
ord-fa02fb31aad7433892df2eaa2335020f
Source dataset
uspto-grants-1986_12
Patent number
US04633025

Reaction notes

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