Methanol → (4-Pyrrolidin-1-yl-cyclohexyl)-methylamine
Reaktionsgleichung
C(OC(=O)NC[CH:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13]1)C1C=CC=CC=1.C([O-])=O.[NH4+:27].[CH3:28]O>>[N:18]1([CH:15]2[CH2:14][CH2:13][CH:12]([NH:27][CH3:28])[CH2:17][CH2:16]2)[CH2:19][CH2:20][CH2:21][CH2:22]1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a solution of (4-pyrrolidin-1-yl-cyclohexylmethyl)-carbamic acid benzyl ester (292 mg, 0.92 mmol) in MeOH (5 mL) was added ammonium formate (0.58 g, 9.20 mmol). The reaction flask was flushed with N2 prior to addition of 10% Pd/C (300 mg). The mixture was heated at 65° C. for 2 h whereupon TLC analysis (silica gel, 95:4.75:0.25 DCM/MeOH/NH4OH) showed complete consumption of 57. After cooling to room temperature the reaction mixture was filtered through a plug of celite in order to remove the Pd catalyst. The filtrate contained (4-pyrrolidin-1-yl-cyclohexyl)-methylamine which was used without further purification in the next step.