Reaktion #45450

Reaktionsgleichung

sodium bicarbonate

triphenylphosphine

carbon tetrabromide

2-formyl -pyrrolidine-1-carboxylic acid tert-butyl ester

→

desired product

Ausbeute 86.0%

tert-butyl (2S)-2-(2,2-dibromovinyl)pyrrolidine-1-carboxylate

Ausbeute 86.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeseparated
2. 2
   TrocknenThe organic phase was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe concentrate was purified by flash chromatography on silica gel using 0-1% methanol/dichloromethane

Vorschrift

A solution of triphenylphosphine (21.1 g, 80.3 mmol) and carbon tetrabromide (13.32 g, 40.16 mmol) in dichloromethane (300 mL) at 0° C. was treated with a solution of 2-formyl -pyrrolidine-1-carboxylic acid tert-butyl ester (4.0 g, 20.08 mmol) in dichloromethane (10 mL) dropwise via syringe. The solution was stirred for 1 hour at room temperature, poured into a saturated sodium bicarbonate solution and separated. The organic phase was dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel using 0-1% methanol/dichloromethane to give 6.13 g (86% yield) of the desired product. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.47 (s, 9H), 1.81 (m, 3H), 2.16 (m, 1H), 3.39 (m, 2H), 4.37 (s, 1H), 6.38 (s, 1H).

Quelle