Yield:940009-03-0 76%

Reaction Conditions:

with hydrogen;platinum(IV) oxide in ethanol at 20; under 760.051 Torr; for 1 h;

Steps:

6

A mixture of 2-[(2-methyl-4-nitrophenoxy)methyl]tetrahydro-2H-pyran (3.6 g, 14.3 mmol) and platinum oxide (0.25 g) in ethanol (100 ml) was hydrogenated at room temperature under atmospheric pressure for 1 hour. After filtration of the catalyst and evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 10 to 50% ethyl acetate in petroleum ether) to give 3-methyl-4-(tetrahydro-2H-pyran-2- ylmethoxy)aniline as an oil (2.4 g, 76%); NMR Spectrum 1.6-1.3 (m, 4H), 1.65 (m, IH), 1.80 (m, IH), 2.03 (s, 3H), 3.35 (m, IH), 3.55 (m, IH), 3.68 (m, IH), 3.77 (m, IH), 3.90 (m, IH), 4.51 (br s, 2H), 6.31 (dd, IH), 6.37 (d, IH), 6.60 (d, IH).

References:

WO2007/63291,2007,A1 Location in patent:Page/Page column 72