Triethylamine → (R)-1-Phenylethanamine (S)-2-(2-oxopyrrolidin-1-yl)butanoate

HRID 601729

Reaktionsgleichung

Reaktionsgleichung von HRID 601729
[CH3:1][C@@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:17]([CH:19]([N:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])[C:20]([OH:22])=[O:21])[CH3:18]>C1(C)C=CC=CC=1>[CH3:1][C@@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]([C@H:19]([N:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])[C:20]([OH:22])=[O:21])[CH3:18]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 104647512-(2-Oxopyrrolidin-1-yl)butanoic acid

Produkt 1

HCID 44140303(R)-1-Phenylethanamine (S)-2-(2-oxopyrrolidin-1-yl)butanoateAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of (R)-alpha-methylbenzylamine (106 g) and triethylamine (89 g) in toluene (100 ml) was added to a suspension of (RS)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid (300 g, 1.75 mol) in toluene (1 L). The mixture was heated until complete dissolution, cooled to room temperature and stirred for 3 hours. The solids were filtered and rinsed with toluene (300 ml) to give 250 g of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-alpha-methylbenzylamine salt. The solids were crystallized from toluene and 205 g (yield 41%) of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid (R)-alpha-methylbenzylamine salt was obtained. The isolated solid was treated with hydrochloric acid solution and the enantiomerically pure (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid could be isolated in 90% yield.

Aufarbeitung

  1. temperatureThe mixture was heated until complete dissolution
  2. filtrationThe solids were filtered
  3. washrinsed with toluene (300 ml)

Quellen und Nachweise

ORD-Eintrag
ord-f6523e3307784bdab6a95afdba9aa4d4
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902380B2

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