Methanol → (1-Benzylpiperidine-3,5-diyl)dimethanol

Temperature

0 °C

To dimethyl 1-benzylpiperidine-3,5-dicarboxylate (1.5 g, 5.15 mmol) in dry THF (30 mL) was added a solution of lithium aluminum hydride in THF (2M, 3.87 mL, 7.73 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 min. then warmed to 23° C. and stirred for 1.5 hour. A solution of methanol (0.5 mL) and (0.25 mL) was added followed by a 15% solution of NaOH (0.250 mL). The mixture was stirred for 1 hour at 23° C. then filtered. The organic material was extracted with ethyl acetate (3×20 mL) and the combined extracts were dried (MgSO4) and concentrated in vacuo to afford 0.91 g (75% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.26-7.35 (5H, m), 3.59 (2H, s), 3.44-3.55 (4 H, m), 3.06 (2 H, dt, J=10.6, 1.8 Hz), 1.88-1.98 (2 H, m), 1.79-1.86 (1 H, m), 1.68 (3 H, m). LCMS (+ESI, M+H+) m/z: 236.

1. temperaturethen warmed to 23° C.
2. stirringstirred for 1.5 hour
3. stirringThe mixture was stirred for 1 hour at 23° C.
4. filtrationthen filtered
5. extractionThe organic material was extracted with ethyl acetate (3×20 mL)
6. dry with materialthe combined extracts were dried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-bd6eaa30b1954179b5293953b1011631

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2