Water → 2-(((1-Benzylpyrrolidin-3-yl)methyl)amino)ethanol

HRID 364047

Reaktionsgleichung

Reaktionsgleichung von HRID 364047
[OH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:11][C:10](=O)[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:14]1([CH2:13][N:9]2[CH2:10][CH2:11][CH:7]([CH2:5][NH:4][CH2:3][CH2:2][OH:1])[CH2:8]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14280883N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 142808882-(((1-Benzylpyrrolidin-3-yl)methyl)amino)ethanolAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 46.66 g (0.178 mole) of N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide in 200 ml of tetrahydrofuran was added dropwise to a slurry of 20.25 g (0.534 mole) of lithium aluminum hydride in 150 ml tetrahydrofuran. The reaction was refluxed three hours, then cooled in an ice bath. The work up consisted of sequential addition of 20 ml water, 20 ml 15% sodium hydroxide then 60 ml water. The reaction was filtered and the precipitate washed with ethanol. The filtrate was concentrated at reduced pressure, the residue taken up in dichloromethane, dried over magnesium sulfate, and the solvent removed at reduced pressure to give 32.31 g of 2-[[[1-(phenylmethyl)-3-pyrrolidinyl]methyl]amino]ethanol as an oil. This material was used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction was refluxed three hours
  2. temperaturecooled in an ice bath
  3. filtrationThe reaction was filtered
  4. washthe precipitate washed with ethanol
  5. concentrationThe filtrate was concentrated at reduced pressure
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b9ddcc7b5ab5480b9ab5e3531e45c1e6
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604401

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