Boron trifluoride etherate → (2S,4S)-4-acetylthio-2-(1,3-dithiolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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).

1. customthe organic layer was separated
2. washwashed with brine
3. dry with materialThe organic layer was dried over magnesium sulfate
4. customevaporated
5. customThe residue was chromatographed on silica gel (50 ml)
6. washeluted with a mixture of acetone and dichloromethane (2:98, V/V)

ORD-Eintrag

ord-4ce6fdb16cdc47aeb1dd914270f8e3ab

Quelldatensatz

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05420122