To a slurry of palladium hydroxide on carbon (1.867 g, 2.66 mmol) in MeOH (250 mL) was added a solution of (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhex-1-ynyl)phenyl)cyclopentanecarboxylate, L-tartaric Acid 2 (25.5 g, 53.2 mmol) in MeOH (50 mL). The reaction mixture was purged with hydrogen and an atmosphere of hydrogen was maintained via balloon. After about 15 hours the reaction mixture was filtered through Celite® and concentrated in vacuo to provide (1R,3R)-methyl 1-amino-3-(4-(6-methoxyhexyl)phenyl)cyclopentanecarboxylate, L-tartaric acid 2 (25.6 g, 52.9 mmol, 100% yield) as a colorless solid.
