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

HRID 846942

Reaction equation

HRID 846942 reaction equation
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH:23]=O)[CH2:6]1)(=[O:3])[CH3:2].[CH2:25]([SH:28])[CH2:26][SH:27].B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([CH:23]2[S:28][CH2:25][CH2:26][S:27]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 18638815(2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 57182042(2S,4S)-4-acetylthio-2-(1,3-dithiolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ac4cafffe8f64141bd4913a57cac9332
Source dataset
uspto-grants-1992_08
Patent number
US05138064

Linked notes

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