N-(tert-Butoxycarbonyl)-D-prolinal → tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate

Participants

Reaction Steps

775 mg of commercially available diethyl 3-chlorobenzylphosphonate are dissolved in 20 ml of THF, and 3 ml of lithium hexamethyldisilazane are added dropwise at −78° C. under protective gas. After 1 h, a solution of 500 mg of tert-butyl-(R)-2-formylpyrrolidine-1-carboxylate in 5 ml of THF is added dropwise at the temperature indicated. The batch is stirred at RT for 3 h and subsequently subjected to aqueous work-up, giving 1 g of tert-butyl (R)-2-[(E)-2-(3-chlorophenyl)vinyl]pyrrolidine-1-carboxylate as colourless oil, which is immediately reacted further.

Provenance & Evidence