Sulfuric Acid → rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 153.2 g (600 mmol) of (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (commercially available from Synthetech Oregon, USA) in 80 mL of EtOAc was dosed to a solution of 65.1 g (630 mmol) of sulfuric acid in 480 mL of EtOAc at 20-25° C. The reaction mixture was stirred for 60 min at 42-48° C. After complete conversion the reaction mixture was cooled to 18-22° C. Then 127.5 g (1260 mmol) of TEA was dosed at 20-30° C. Finally 100 mL of DMF was added. The reaction mixture was used in the next step immediately after preparation.

Provenance & Evidence