Hydrochloric Acid → Octahydrofuro(3,4-c)pyridine

Temperature

95 °C

Tert-butyl 3,4-bis(hydroxymethyl)piperidine-1-carboxylate (1.00 g, 4 mmol) and concentrated hydrochloric acid (8 mL) were added to a sealed tube (50 mL). The reaction mixture was heated at 95° C. overnight, cooled to room temperature and concentrated in vacuo. The pH was adjusted to 8 by adding aqueous solution of NaOH. The mixture was extracted with CH2Cl2 (30 mL×2). The organic phase was washed with water (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to afford the crude product as yellow oil (300 mg, 52.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 128.2 (M+1).

1. temperaturecooled to room temperature
2. concentrationconcentrated in vacuo
3. additionby adding aqueous solution of NaOH
4. extractionThe mixture was extracted with CH2Cl2 (30 mL×2)
5. washThe organic phase was washed with water (30 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-375564d921a0412b8b83f2c5b8b7885f

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181277B2