Trifluoroacetic acid → 4-(Azetidin-3-yl)piperazin-2-one

HRID 1922660

Reaktionsgleichung

Reaktionsgleichung von HRID 1922660
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)[CH2:11]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 596054391-Boc-3-(3-oxo-1-piperazinyl)azetidine

Produkt 1

HCID 596061454-(Azetidin-3-yl)piperazin-2-oneAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-(3-oxopiperazin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (400 mg, 1.57 mmol) and TFA (3 mL) in DCM (6 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording 4-Azetidin-3-ylpiperazin-2-one as a white solid (227 mg, 93%). 1H NMR (CDCl3, 300 MHz): δ 6.08 (s, 1H); 3.63-3.56 (m, 3H); 3.42-3.35 (m, 3H); 3.31 (t, J=6.74 Hz, 1H); 3.03 (s, 2H); 2.59-2.51 (m, 2H).

Aufarbeitung

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-003036c116c1432885becedb6ba8aa46
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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