Yield:-

Reaction Conditions:

Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanonewith titanium(IV) isopropylate;ammonia in methanol at 20; for 6 h;
Stage #2: with sodium tetrahydroborate in methanol;

Steps:

28

Preparation 28 l-(6-Methylpyridin-3-yl)ethanamineStir a mixture of l-(6-methylpyridin-3-yl)-ethanone (10 g, 74 mmol) in titanium tetra(isopropoxide) (42.1 g, 148 mmol) and ammonia (370 mmol, 2 M in methanol) under N₂ for 6 h at RT. To this mixture add sodium tetrahydroborate (4.2 g, 111 mmol) and stir overnight. Quench the reaction mixture with ammonium hydroxide and filter the mixture. From the filtrate, remove the solvent and extract the residue with DCM, wash with saturated aqueous sodium chloride and dry over Na₂SO₄, filter, and remove the solvent to obtain the title compound as a dark yellow oil (8.16 g). MS (ES) m/z 137 [M+ 1]⁺ .

References:

WO2008/144222,2008,A2 Location in patent:Page/Page column 17