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

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Reaction Steps

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.

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