Reaktion #166965

Reaktionsgleichung

2-bromo-1-(6-bromonaphthalen-2-yl)-ethanone

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

triethylamine

→

pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

Ausbeute 84.3%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Sonstigeevaporated under vacuum
3. 3
   workup.DISSOLUTIONOil was dissolved in dichloromethane (100 mL)
4. 4
   Extraktionextracted with water (50 mL) and with NaHCO3 solution (50 mL)
5. 5
   Sonstigeevaporated under vacuum to a concentrated liquid
6. 6
   SonstigeSolution was purified by chromatography (0-30% ethyl acetate:hexane)
7. 7
   Sonstigeevaporated under vacuum

Vorschrift

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (24.0 g) was dissolved in acetonitrile (330 mL), and triethylamine (15.6 mL) was added. A solution of 2-bromo-1-(6-bromonaphthalen-2-yl)-ethanone (33.0 g) in acetonitrile (170 mL) were added. Reaction mixture was stirred over 3 days and evaporated under vacuum. Oil was dissolved in dichloromethane (100 mL), extracted with water (50 mL) and with NaHCO3 solution (50 mL), and evaporated under vacuum to a concentrated liquid. Solution was purified by chromatography (0-30% ethyl acetate:hexane) and evaporated under vacuum, giving pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester (39.2 g, 84%) as a tan solid.

Quelle