3-Hydroxy-2-(pyrrolidinomethyl)-pyridine → 2-(Pyrrolidin-1-yl)methyl-3-hydroxy piperidine

A mixture of 2-(pyrrolidinylmethyl)-3-pyridinol (21.0 g) and platinum oxide (1.0 g) in glacial acetic acid (120 ml) was hydrogenated a 70 psi and room temperature for 20 h. Further platinum oxide (1.0 g) was then added and hydrogenation continued at 70 psi for a further 24 h. The reaction mixture was filtered, the combined filtrates were concentrated in vacuo and the residue was dissolved in water (200 ml). This solution was acidified to pH1 with 5M hydrochloric acid before washing with dichloromethane (2×70 ml). The aqueous layer was then basified (pH14) with 5M aqueous sodium hydroxide before extracting with dichloromethane (3×70 ml). The combined extracts were washed with 2M aqueous sodium hydroxide (50 ml) and water (50 ml), dried and concentrated in vacuo to give an oil. This crude product was distilled at reduced pressure (Kughelrohr oven, 140°, 0.8 mm Hg) to give the title compound as a waxy solid, (6.17 g) m.p. 45°-50°.

1. customa 70 psi and room temperature
2. customfor 20 h
3. filtrationThe reaction mixture was filtered
4. concentrationthe combined filtrates were concentrated in vacuo
5. dissolutionthe residue was dissolved in water (200 ml)
6. washbefore washing with dichloromethane (2×70 ml)
7. extractionbefore extracting with dichloromethane (3×70 ml)
8. washThe combined extracts were washed with 2M aqueous sodium hydroxide (50 ml) and water (50 ml)
9. customdried
10. concentrationconcentrated in vacuo
11. customto give an oil
12. distillationThis crude product was distilled at reduced pressure (Kughelrohr oven, 140°, 0.8 mm Hg)

ORD record

ord-5d20e767ee8b44b08ae0c9cc93d2c4b3

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05114945