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

HRID 1720478Notes

Reaction equation

HRID 1720478 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH:29]1[O:31][CH2:30]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CO>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH:29]([OH:31])[CH2:30][S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57093261(2S)-1-(t-Butoxycarbonyl)-2-[1-hydroxy-2-(4-methoxyphenylthio)ethyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Methoxythiophenol (1.0 ml) and triethylamine (1.0 ml) were added to (2S)-1-(t-butoxycarbonyl)-2-(1,2-epoxyethyl)-pyrrolidine (1.57 g) as obtained in Example 1-A) in methanol (50 ml), and the mixture was stirred for 1.5 hours under reflux. The reaction mixture was concentrated and the residue was poured into ice-water, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated. The residue was recrystallized from a mixted solution of hexane-ethyl acetate to give 2.16 g of the title compound as colorless needles.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was poured into ice-water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from a mixted solution of hexane-ethyl acetate

Sources & evidence

ORD record
ord-76d846755dfc4b40a425695094a3441a
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

Loading…