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

Participants

Reaction Steps

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.

Provenance & Evidence