Sodium Cyanide → HCID 68681909, compound

Participants

Reaction Steps

A mixture of the triflate (A2) (447 mg, 1 mmol), sodium cyanide (100 mg, 2 mmol), copper (I) iodide (19 mg, 0.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) in acetonitrile (10 ml) was degassed and heated under reflux under nitrogen for 4 h. After concentration, the residue was directly purified by flash chromatography (hexane/EtOAc 8:2) to give tert-butyl 4-cyano-2H-spiro[naphthalene-1,4′-piperidine]-1′-carboxylate (A3) (300 mg). LC-MS: m/e=269.0 (M+H−C(CH3)3. Rt=3.75 min. 1H-NMR (500 MHz, DMSO-d6): 7.49 (d, 1H), 7.42-7.36 (m, 3H), 7.09 (t, 1H), 3.81 (br. d, 2 H), 3.03 (br. s, 2H), 2.67 (d, 2H), 1.70 (td, 2H), 1.62 (d, 2H), 1.41 (s, 9H),

Provenance & Evidence