Hydrochloric Acid → Ethyl 5-hydroxypiperidine-3-carboxylate

Anhydrous HCl was bubbled through a suspension of (±)-5-hydroxypiperidine-3-carboxylic acid (5.6 g, 38.6 mmol) (according to the procedures as disclosed in J. Med. Chem., 25, 1157-1162, (1982)), cooled to 0° C. in EtOH (100 mL), until saturation was reached. The reaction mixture was warmed to room temperature, stirred overnight, then concentrated in vacuo. The crude salt was cooled to 0° C. in CHCl3 (80 mL), and anhydrous NH3 was bubbled through the solution. The resulting white precipitate was removed by vacuum filtration, and the filtrate was concentrated in vacuo to provide 6.6 g (99%) of (±) ethyl 5-hydroxypiperidine-3-carboxylate as a pale yellow oil.

1. concentrationconcentrated in vacuo
2. temperatureThe crude salt was cooled to 0° C. in CHCl3 (80 mL)
3. customanhydrous NH3 was bubbled through the solution
4. customThe resulting white precipitate was removed by vacuum filtration
5. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-c0d6f99574bc48d0b796dae15299ee72

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953805B2