Thiophenol → (2S)-1-(t-butoxycarbonyl)-2-[1-hydroxy-2-(phenylthio)ethyl]pyrrolidine

HRID 1720468Notes

Reaction equation

HRID 1720468 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]1[O:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:15])[CH2:14][S:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 15297814(2S)-1-(t-butoxycarbonyl)-2-[1-hydroxy-2-(phenylthio)ethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (2S)-1-(t-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (3.00 g) in methanol (100 ml) were added thiophenol (1.5 ml) and triethylamine (2.0 ml), followed by 2 hour' stirring under reflux. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate) to give 4.14 g of (2S)-1-(t-butoxycarbonyl)-2-[1-hydroxy-2-(phenylthio)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-ed64fa5f3adf4b7a8ba1464d5bd750a4
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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