(3-Morpholinopyridin-2-yl)Methanol synthesis

Yield:1126367-65-4 98%

Reaction Conditions:

with sodium tetrahydroborate in methanol at 0 - 25; for 0.166667 h;

Steps:

137.137b

A mixture of 3-morpholinopicolinaldehyde (400 mg, 2.08 mmol) in MeOH (15 mL) was cooled to 0⁰C. NaBH₄ (55.1 mg, 1.46 mmol) was added in one portion. The mixture was stirred at RT for 10 min after which 2N NaOH (ImL) was added to the mixture. After concentration in vacuo, the residue was purified with ISCO MPLC (40-100% EtOAc/hexane) to yield the title compound as a white solid (398 mg, 98 %). ¹HNMR (DMSO-d₆) 8.25 (d, IH), 7.50 (d, IH), 7.29 (m, IH), 5.00 (t, IH), 4.56 (d, 2H), 3.78 (m, 4H), 3.89 (m, 4H). MS (M+H⁺) = 195.

References:

WO2009/27746,2009,A1 Location in patent:Page/Page column 116-117