Formaldehyde → (2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidine

HRID 1030167

Reaktionsgleichung

Reaktionsgleichung von HRID 1030167
C=O.[C:3]([BH3-])#[N:4].[Na+].[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14]N1)=[O:11])[CH3:8].[OH-].[Na+].[Cl-].[Na+]>C(#N)C>[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][N:4]1[CH3:3])=[O:11])[CH3:8]

Komponenten

7

Edukt 5

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 14880286(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

Produkt 1

HCID 10590942(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)-1-methylpyrrolidineAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3.43 ml of 35% formalin and 804 mg of sodium cyanoborohydride were added to a solution of 2.36 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)-pyrrolidine dissolved in 42 ml of acetonitrile, and the mixture was stirred at room temperature for 40 minutes. At the end of this time, a 1N aqueous solution of sodium hydroxide was added, and the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with ethyl acetate) to afford 1.93 g of the title compound as colorless crystals. Infrared Absorption Spectrum (KBr) δmax cm-1 : 1655, 1513, 1252.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel (eluted with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d77b6f030c554bc8a2ad741dcc154e99
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104867

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