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

HRID 1720478
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1720478
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-76d846755dfc4b40a425695094a3441a
Quelldatensatz
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05506256

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