4-Methylmorpholine → 2-(1-Pyrrolidinyl)carbonyl-1-benzylpyrrolidine

HRID 369882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369882
[CH2:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N:17]1[CH2:22][CH2:21]O[CH2:19][CH2:18]1.ClC(OCC(C)C)=O.N1CCCC1>ClCCl>[N:17]1([C:10]([CH:9]2[CH2:13][CH2:14][CH2:15][N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:12])[CH2:22][CH2:21][CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 728719N-Benzyl-L-proline

Produkt 1

HCID 232826462-(1-Pyrrolidinyl)carbonyl-1-benzylpyrrolidineAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-benzyl-L-proline (50 g) in dichloromethane (300 ml) is cooled with ice. To the solution is added N-methylmorpholine (22.5 g), and then further thereto is added dropwise isobutyl chloroformate (30 g). The mixture is stirred at the same temperature for about one hour, and thereto is added dropwise pyrrolidine (18.8 ml) at the same temperature. The mixture is warmed to room temperature, and stirred for two days. The mixture is washed twice with water (250 ml), and dried over magnesium sulfate. The mixture is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetate-n-hexane to give 2-(1-pyrrolidinyl)carbonyl-1-benzylpyrrolidine (31 g), as white powder.

Aufarbeitung

  1. stirringstirred for two days
  2. washThe mixture is washed twice with water (250 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe residue is recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-520efe8c1c574273821a2b313e60c990
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140330

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