تفاعل #65546

معادلة التفاعل

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe organic layer was separated
2. 2
   غسيلwashed with brine
3. 3
   تجفيفThe organic layer was dried over magnesium sulfate
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue was chromatographed on silica gel (50 ml)
6. 6
   غسيلeluted with a mixture of acetone and dichloromethane (2:98, V/V)

الإجراء التجريبي

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).

المصدر