3-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acrylic acid synthesis

Yield:-

Reaction Conditions:

in tetrahydrofuran;water;

Steps:

R.3 Preparation of 3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-ethylsulfanyl-N-phenylethylpropanamide

To a stirred suspension of the crude 2-(2-ethoxycarbonyl-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (136 mg) in THF (1 ml) and H₂O (1 ml) was added LiOH.H₂O (48 mg, 1.14 mmol) at room temperature. The mixture was stirred at room temperature for 17 hr. The mixture was extracted with 1N NaOH and AcOEt. The aqueous layer was acidified with 1N HCl, extracted with AcOEt, washed with saturated aqueous NaCl, dried (MgSO₄), and concentrated in vacuo to give 2-(2-carboxy-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a crude oil (109 mg).

References:

US2003/55002,2003,A1