Ethyl cyanoacetate → 1-(Cyanoacetyl)pyrrolidine
Reaktionsgleichung
[C:1]([CH2:3][C:4]([O:6]CC)=O)#[N:2].[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>>[O:6]=[C:4]([N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:3][C:1]#[N:2]Komponenten
3
Versuchsvorschrift
Ethyl cyanoacetate (5.33 mL, 50 mmol) and pyrrolidine (20.87 mL, 250 mmol) were gently refluxed at 90° C. in an oil bath for 8 hours. Excess pyrrolidine was removed by concentration and the residue was triturated with diethyl ether. This was purified by silica gel column chromatography eluting with 50% acetone in n-hexane to provide the desired product (5.0 g). MS (DCI) m/e 139 (M+H)+, 156 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 3.90 (s, 2H), 3.27-3.38 (m, 4H), 1.73-1.91 (m, 4H).
Aufarbeitung
- customExcess pyrrolidine was removed by concentration
- customthe residue was triturated with diethyl ether
- customThis was purified by silica gel column chromatography
- washeluting with 50% acetone in n-hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-36d6b918c95a40108c255e7d5d65b832
- Quelldatensatz
- uspto-grants-2009_02
- Patentnummer
- US07491718B2
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