Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate → Ethyl 4-amino-2-methylcyclopentanecarboxylate
Reaktionsgleichung
C([N:8](CC1C=CC=CC=1)[CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH3:19])[CH2:10]1)C1C=CC=CC=1>CCO>[NH2:8][CH:9]1[CH2:13][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]([CH3:19])[CH2:10]1Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a vessel containing a slurry of 20% wet Pd(OH)2—C (5.00 g, 35.6 mmol) in EtOH (355 mL) was added ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate (50.0 g, 142 mmol). The reaction was shaken for about 60 min at about 50° C. under about 30 psi of H2. The resulting mixture was filtered through a pad of Celite® and the filtrate was concentrated under reduced pressure to give ethyl 4-amino-2-methylcyclopentanecarboxylate (23.5 g, 96%) as a yellow oil: 1H NMR (CDCl3) δ 4.24-4.02 (m, 2H), 3.41-3.27 (m, 1H), 2.81 (dd, J=7.6, 15.4 Hz, 1H), 2.36-2.20 (m, 1H), 2.21-2.02 (m, 4H), 1.81-1.69 (m, 1H), 1.33-1.15 (m, 4H), 0.98 (d, J=7.0 Hz, 3H).