Acetic Acid → (3S)-3-(4-Methoxybenzylthio)-1-methylpyrrolidine

HRID 1030149

Reaktionsgleichung

Reaktionsgleichung von HRID 1030149
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][S:8][C@H:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.C=O.[C:18](O)(=O)C.C(OCC)(=O)C>C(#N)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C@H:9]2[CH2:13][CH2:12][N:11]([CH3:18])[CH2:10]2)=[CH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 14880282HCID 14880282, Verbindung

Produkt 1

HCID 57243155(3S)-3-(4-Methoxybenzylthio)-1-methylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

750 mg of (3S)-3-(4-methoxybenzylthio)pyrrolidine [which had been prepared by neutralization of 900 mg of (3S)-3-(4-methoxybenzylthio)pyrrolidine hydrochloride, prepared as described in step (3) above, with sodium bicarbonate] were dissolved in 15 ml of dry acetonitrile, and 1.44 ml of a 35% by volume solution of formaldehyde in water was added to the solution. The reaction mixture was then stirred for 15 minutes, after which it was neutralized by the addition of acetic acid; it was then again stirred for a further 2.5 hours. At the end of this time, the reaction mixture was poured into 200 ml of ethyl acetate, and the mixture was washed with a 2N aqueous solution of potassium hydroxide and an aqueous solution of sodium chloride. The organic layer was dried over potassium carbonate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 3:1 by volume mixture of ethyl acetate and methanol), to afford 349 mg of the title compound as a colorless oil.

Aufarbeitung

  1. stirringit was then again stirred for a further 2.5 hours
  2. washthe mixture was washed with a 2N aqueous solution of potassium hydroxide
  3. dry with materialThe organic layer was dried over potassium carbonate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel (
  6. washeluted with a 3:1 by volume mixture of ethyl acetate and methanol),

Quellen und Nachweise

ORD-Eintrag
ord-15ea8125c7bd4efcb6fbffe313c03027
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104867

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