Hydrochloric Acid → HCID 89739579, compound

To a solution of methyl 3-methylpicolinate (5 g) and 36% HCl (2 eq) in methanol was added 10% Pd/C. The Parr shaker bottle was evacuated/H2 purged 3×, and then shaken at 50 psi until starting material was consumed (typically <1 h). The reaction was filtered through diatomaceous earth and concentrated to yield methyl 3-methylpiperidine-2-carboxylate hydrochloride salt without further purification. To a suspension of LiAlH4 (4 eq) in THF (40 ml) was added in portions the above crude salt at 0° C. The reaction was allowed to stir to rt overnight and then refluxed for 2 h. The reaction mixture was then quenched with saturated Na2SO4 at 0° C. and stirred for 1 h. The reaction mixture was filtered and concentrated in vacuo to give the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) δ 3.4 (m, 2H), 2.9 (m, 1H), 2.8 (m, 1H), 2.6 (m, 1H), 1.7 (m, 1H), 1.6-1.4 (m, 4H), 0.8 (d, 3H).

1. customThe Parr shaker bottle was evacuated/H2
2. custompurged 3×
3. customwas consumed (typically <1 h)
4. filtrationThe reaction was filtered through diatomaceous earth
5. concentrationconcentrated

ORD record

ord-651abb6d991b43fc9351919dfdd1464b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440982B2