Morpholine → 4-((5-Oxo-2-pyrrolidinyl)carbonyl)morpholine

HRID 1500408

Reaktionsgleichung

Reaktionsgleichung von HRID 1500408
CO[C:3](=[O:10])[C@@H:4]1[CH2:8][CH2:7][C:6](=[O:9])[NH:5]1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1(C)C(C)=CC=CC=1>[N:11]1([C:3]([CH:4]2[NH:5][C:6](=[O:9])[CH2:7][CH2:8]2)=[O:10])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 78646Methyl 5-oxo-L-prolinate

Produkt 1

HCID 1035684-((5-Oxo-2-pyrrolidinyl)carbonyl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 143 g of pyroglutamic acid methyl ester (1 mol) and 139 g morpholine (1.60 mol) in 900 ml of xylene is heated to 140° C. for 20 h. The xylene is evaporated to a volume of 500 ml. From the suspension obtained, the precipitate is filtered off, washed with THF to yield the desired compound after drying in vacuo. From the filtrate the solvent is evaporated completely. This crude product [(R/S)-5-(morpholine-4-carbonyl)pyrrolidin-2-one] is filtered over 800 g silica gel with THF as the solvent and evaporated to dryness to yield a second crop of the desired compound. This compound is used directly in the next step. HPLC analysis shows the material to be in an enantiomeric ratio: 55.8:44.2 [(4-a, R1=H; R4=morpholine): (4-b, R1=H; R4=morpholine), respectively].

Aufarbeitung

  1. customThe xylene is evaporated to a volume of 500 ml
  2. customFrom the suspension obtained
  3. filtrationthe precipitate is filtered off
  4. washwashed with THF

Quellen und Nachweise

ORD-Eintrag
ord-1de717f7ef9d4813acf666bae4fd9833
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206116B2

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