Methyl iodide → tert-Butyl benzyl(4-iodobutyl)carbamate

To a solution of benzyl-(4-hydroxy-butyl)-carbamic acid tert butyl ester (6.06 g 21.7 mmol) in acetonitrile (25 mL), carbonyldiimidazole (3.52 g 21.7 mmol) and iodomethane (6.8 mL 109 mmole) were added. The reaction mixture became lukewarm and was stirred for an hour at room temperature followed by another 2 h under reflux. The reaction mixture was allowed to cool to room temperature and additional iodomethane (6.8 mL) was added and the reaction was refluxed for an additional hour. The reaction mixture was allowed to cool to room temperature and was diluted with diethyl ether (150 mL) resulting in a white suspension that was washed with of water (100 mL). The organic layer was washed successively with, 1N HCl (50 mL), saturated NaHCO3 (50 mL), 5% Na2S2O3 (50 mL), and brine. The organic layer was dried on Na2SO4 and the resulting yellow oil crude was purified by flash chromatography using a 95:5 mixture of ethyl acetate-petroleum ether as eluent to give N-benzyl-N-(t-butoxycarbonyl)-4-amino-1-iodobutane (4.49 g, 53%) as colorless, viscous oil. 1H NMR (CDCl3) δ 7.24-7.35 (m, 5H); 4.42 (bs, 2H); 3.19 (bs, 4H); 1.76 (bs, 2H); 1.6 (bs, 2H); 1.51 (s, 9H).

1. temperatureunder reflux
2. temperatureto cool to room temperature
3. temperaturethe reaction was refluxed for an additional hour
4. temperatureto cool to room temperature
5. customresulting in a white suspension that
6. washwas washed with of water (100 mL)
7. washThe organic layer was washed successively with, 1N HCl (50 mL), saturated NaHCO3 (50 mL), 5% Na2S2O3 (50 mL), and brine
8. customThe organic layer was dried on Na2SO4
9. customthe resulting yellow oil crude was purified by flash chromatography
10. additiona 95:5 mixture of ethyl acetate-petroleum ether as eluent

ORD record

ord-053c7bfdf97f4ca0813ba3d066ea43fe

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872827B2