Methyl iodide → 4-Cbz-1-methyl-2-piperazinone

HRID 646932

Reaktionsgleichung

Reaktionsgleichung von HRID 646932
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]C([O-])(C)C.[K+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH3:18])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 586385404-Cbz-1-methyl-2-piperazinoneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-oxo-piperazine-1-carboxylic acid benzyl ester (2.00 g, 8.54 mmol) in DMF (30 mL) was added KOtBu (1.54 g, 13.7 mmol) under Ar. The resulting solution was stirred at room temperature for 15 min and cooled to 0° C. MeI (0.85 mL, 14 mmol) was then added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. DMF was removed in vacuo and the residue was chromatographed on silica (5-50% EtOAc:hexane) to obtain the title compound (1.40 g, 66%). 1H-NMR (CDCl3; 400 MHz): δ 7.32 (m, 5H), 5.13 (s, 2H), 4.13 (s, 2H), 3.70 (m, 2H), 3.34 (m, 2H), 2.97 (s, 3H)

Aufarbeitung

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 h
  4. customDMF was removed in vacuo
  5. customthe residue was chromatographed on silica (5-50% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ebc6365f48494669a8f43f49246418fa
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705042B2

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