Ethyl 4-(dibenzylamino)-2-methylcyclopentanecarboxylate → Ethyl 4-amino-2-methylcyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence