Triethylamine → (2S)-1-(t-Butoxycarbonyl)-2-[1-hydroxy-2-(4-nitrophenylthio)-ethyl]pyrrolidine

HRID 1720481Notes

Reaction equation

HRID 1720481 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH:30]1[O:32][CH2:31]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CO>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH:30]([OH:32])[CH2:31][S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 158094-NitrobenzenethiolHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 22860062(2S)-1-(t-Butoxycarbonyl)-2-[1-hydroxy-2-(4-nitrophenylthio)-ethyl]pyrrolidineYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Nitrothiophenol (1.21 g) and triethylamine (0.91 ml) were added to (2S)-1-(t-butoxycarbonyl)-2-(1,2-epoxyethyl)-pyrrolidine (1.39 g) as obtained in Example 1-A) in methanol (50 ml), and the mixture was stirred for 2 hours under reflux. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluate : hexane-ethyl acetate) to give 1.85 g of the title compound. B) (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2-(4-nitrophenylthio)ethyl]pyrrolidine

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (eluate : hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cc75a27a8f2b4004a3eab8bb1cc5d183
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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