Triethylamine → (S)-tert-Butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate

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Reaction Steps

Triethylamine (14.6 ml) and ethyl chloroformate (10.6 ml) were added to a solution of N-(tert-butoxycarbonyl)-L-proline (21.5 g) in THF (330 ml) at -20° C., and the mixture was stirred for 30 minutes. Then, diazomethane (0.6M, diethyl ether solution, 120 ml) was added, and the mixture was stirred overnight. Toluene was added to the reaction mixture, washed with a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (26.2 g).

Provenance & Evidence