Acetic Acid → Methyl 3-Amino-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

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Reaction Steps

A solution of methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate (6.5 g, Reference Example 15) in ethanol (100 ml) was treated with 20% palladium hydroxide on charcoal (1.0 g), acetic acid (3.6 ml) and water (10 ml) and the mixture was hydrogenated at room temperature overnight. The spent catalyst was removed by filtration through Celite and the filtrate was evaporated to low bulk. The residue was taken up in ether and this solution was washed with aqueous sodium bicarbonate solution, and the layers separated. The aqueous layer was extracted twice with fresh ether and the combined ether extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of methanol and dichloromethane (1:9, v/v) to give the title compound (1.7 g) as a clear oil which slowly crystallised on standing. MS (ES+) 335 (MH+), 357 (MNa+), 669 (2MH+).

Provenance & Evidence