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

D-proline (5 g, 43.4 mmol) was dissolved in 2 M NaOH (26 ml) and cooled in an ice bath, and the solution was diluted with acetone (26 ml). An acetone solution (26 ml) of methacryloyl chloride (6.3 ml, 65.1 mmol) and a 2 M NaOH solution (34 ml) were simultaneously added over a period of 1 h to the solution of D-proline. After addition the resulting mixture was stirred for 3 h at room temperature. The mixture was evaporated at 40° C., extracted with ether (2×40 ml) and acidified to pH 2 with concentrated HCl. The resulting mixture was extracted with ethyl acetate (3×50 ml), dried over Na2SO4 and evaporated. The yield was 11.5 g (theoretical 8.0 g), and it was used without further purifications.

1. temperaturecooled in an ice bath
2. additionAfter addition the resulting mixture
3. customThe mixture was evaporated at 40° C.
4. extractionextracted with ether (2×40 ml)
5. extractionThe resulting mixture was extracted with ethyl acetate (3×50 ml)
6. dry with materialdried over Na2SO4
7. customevaporated

ORD record

ord-2285527e19774305ace3b3423ecb67ab

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07390923B2