反应详情

A mixture of butyl cis-4-(azidomethyl)cyclohexanecarboxylate (27.85 g, 116 mmol), 6N hydrochloric acid (39 ml, 234 mmol) and 10% palladium on carbon (3.78 g) in ethanol (500 ml) was hydrogenated (hydrogen balloon) for 2.5 days. The catalyst was removed by filtration through Celite. The filter cake was washed with ethanol (3×50 ml) and the filtrate was concentrated under reduced pressure to give a gum. The gum was taken up in water (250 ml) and washed with ether (250 ml). The aqueous layer was basified to pH 10 with 10N sodium hydroxide solution and extracted with ethyl acetate (3×250 ml). The ethyl acetate layer was washed with water (100 ml) and brine (100 ml), dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give butyl cis-4-(aminomethyl)cyclohexanecarboxylate (15.25 g, 62%) as a gum: 1H NMR (CDCl3) 4.08 (2H, t, J 7 Hz), 2.57 (2H, d, J 8 Hz), 2.02 (2H, m), 1.66-1.51 (6H, m), 1.45-1.23 (5H, m), 0.94 (3H, t, J 7 Hz). MS: 214.2 (M+1).

1. customfor 2.5 days
2. customThe catalyst was removed by filtration through Celite
3. washThe filter cake was washed with ethanol (3×50 ml)
4. concentrationthe filtrate was concentrated under reduced pressure
5. customto give a gum
6. washwashed with ether (250 ml)
7. extractionextracted with ethyl acetate (3×250 ml)
8. washThe ethyl acetate layer was washed with water (100 ml) and brine (100 ml)
9. dry with materialdried (sodium sulfate)
10. filtrationfiltered
11. customthe solvent was evaporated under reduced pressure