Yield:58088-67-8 59%

Reaction Conditions:

with ammonium acetate;sodium cyanotrihydridoborate in methanol at 20;

Steps:

14

To a solution of 2-acetyl-6-methylpyridine (4.7g, 34.8mmol) in anhydrous methanol (100ml) was added ammonium acetate (26.8g, 348mmol) and sodiumcyanoborohydride (1.75g, 27.8mmol) and the resulting mixture stirred at RT overnight. The mixture was evaporated and the residue dissolved in water and basified by the addition of KOH and extracted with DCM (x 3). The DCM layers were combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by columnchromatography on silica to afford the title compound (i-14) (eluent: 5% MeOH in DCM) to give 2.8g (59%) as a clear oil. ¹H NMR (CDCl₃): 1.41 (d, J 6.7 Hz, 3H), 1.78 (brs, 2H), 2.54 (s, 3H)₅ 4.21 (q, J6.7 Hz, 1H), 6.99 (d, Jl.6 Hz, 1H), 7.09 (d, J7.7 Hz, 1H), 7.52 (m, 1H).

References:

WO2011/25774,2011,A1 Location in patent:Page/Page column 49-50