Ethyl Acetate → HCID 67366133, Verbindung

HRID 2387951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2387951
[C:1](Cl)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([N:19]1[CH2:24][CH2:23][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:21][CH2:20]1)C1C=CC=CC=1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[CH2:4]([O:3][C:1]([N:19]1[CH2:20][CH2:21][C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:23][CH2:24]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67367347HCID 67367347, Verbindung

Produkt 1

HCID 67366133HCID 67366133, VerbindungAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

60 g (3.5 equiv.) of Cbz chloride were added dropwise over a period of 10 minutes to a solution of 33 g (1 equiv.) of 1-benzyl-4-phenyl-4-(pyrrolidin-1-yl)piperidine in 330 ml of chloroform, and the resulting reaction mixture was stirred for 30 minutes at room temperature. The progress of the reaction was monitored by thin-layer chromatography (ethyl acetate). When the reaction was complete, the solvent was distilled off completely and the residue was adjusted to ˜pH 6 with 10% HCl solution and washed 3× with 100 ml of EtOAc. In an ice bath, the aqueous solution was adjusted to ˜pH 9 with NaOH solution and then extracted 3× with 100 ml of chloroform. The combined organic phases were dried with Na2SO4. After removal of the solvent under reduced pressure, purification was carried out by column chromatography (silica gel; 20% EtOAc/heptane). 11 g (29%) of product were obtained in the form of a yellow solid.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. distillationthe solvent was distilled off completely
  3. washwashed 3× with 100 ml of EtOAc
  4. customIn an ice bath, the aqueous solution was adjusted
  5. extractionextracted 3× with 100 ml of chloroform
  6. dry with materialThe combined organic phases were dried with Na2SO4
  7. customAfter removal of the solvent
  8. customunder reduced pressure, purification

Quellen und Nachweise

ORD-Eintrag
ord-159fc92ba8014464958e56c946da96c6
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269000B2

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