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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence