Réaction #65546

Équation de réaction

sodium hydrogen carbonate

(2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

1,2-ethanedithiol

boron trifluoride etherate

→

(2S, 4S)-4-acetylthio-2-(1,3-dithiolan-2-yl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe organic layer was separated
2. 2
   Lavagewashed with brine
3. 3
   SéchageThe organic layer was dried over magnesium sulfate
4. 4
   Autreevaporated
5. 5
   AutreThe residue was chromatographed on silica gel (50 ml)
6. 6
   Lavageeluted with a mixture of acetone and dichloromethane (2:98, V/V)

Mode opératoire

To a solution of (2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.00 g) and 1,2-ethanedithiol (0.36 ml) in dichloromethane (20 ml) was added boron trifluoride etherate (0.1 ml), and the solution was stirred for 14 hours at ambient temperature. To the mixture was added saturated aqueous sodium hydrogen carbonate and the organic layer was separated, and washed with brine. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (50 ml) and eluted with a mixture of acetone and dichloromethane (2:98, V/V) to give (2S, 4S)-4-acetylthio-2-(1,3-dithiolan-2-yl) -1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.14 g).

Source