Reaktionsgleichung
C(O)(=O)C.Cl.[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11]1)=[O:9]>C(#N)C>[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]1)=[O:9]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Add acetic acid saturated with HCl(g) (100 mL, ˜3N in HCl) to 3-(trityl-amino)-piperidine-1-carboxylic acid methyl ester (6.51 g, 16.2 mmol). Stir the solution vigorously at room temperature for 2 hours. Concentrate the reaction, follow this by addition of acetonitrile and concentration to assist in the removal of acetic acid (×2). Partition the resulting material between 1N HCl and ethyl acetate, separate the layers, extract the organic layer with 1N HCl. Basify the combined aqueous layers with 5N sodium hydroxide, extract with 20% isopropanol/chloroform (×3). Dry the combined organic layers over magnesium sulfate and concentrate to give 2.45 g of the title compound as a white solid, 95% yield. 1H NMR: consistent with structure. MS (ion spray) 158 (M+).
Aufarbeitung
- concentrationConcentrate
- customthe reaction
- customto assist in the removal of acetic acid (×2)
- customPartition the resulting material between 1N HCl and ethyl acetate
- customseparate the layers
- extractionextract the organic layer with 1N HCl
- extractionextract with 20% isopropanol/chloroform (×3)
- dry with materialDry the combined organic layers over magnesium sulfate
- concentrationconcentrate
Quellen und Nachweise
- ORD-Eintrag
- ord-8d411f7d4713493f87e38178998d2b8d
- Quelldatensatz
- uspto-grants-2006_09
- Patentnummer
- US07101891B2
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