Carbamic acid, [(tetrahydro-2H-pyran-4-yl)methyl]-, 1,1-dimethylethyl ester synthesis

Yield:666262-72-2 91%

Reaction Conditions:

with triethylamine in tetrahydrofuran; for 1 h;Cooling with ice;

Steps:

215.1

To a solution of 4-aminomethyltetrahydropyran (500 mg, 4.4 mmol) in 5.0 mL of tetrahydrofuran was added triethylamine (537 mg, 5.3 mmol) and di-tert-butyl dicarbonate (1.0 g, 4.6 mmol) under ice-cooled conditions. After being stirred for 1 h, the reaction mixture was added water, and diluted with ethyl acetate. The separated organic layer was washed with brine, and dried over Na₂SO₄. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80120 to 50/50) to obtain the title compound (855 mg, 91%).¹H-NMR (CDCl₃) δ(ppm): 1.2-1.4 (m, 2H), 1.44 (s, 9H), 1.6-1.8 (m, 3H), 3.02 (t, J=6.4 Hz, 1H), 3.37 (br t, J=11 Hz, 2H), 3.97 (dd, J=4.11 Hz, 2H), 4.62 (br s, 1H).

References:

US2011/294850,2011,A1 Location in patent:Page/Page column 44