Hydroxyacetonitrile → HCID 57447694, compound

Participants

Reaction Conditions

Reaction Steps

Et3N (7.0 mL, 50 mmol) was added to a suspension of 3-methoxypiperidine hydrochloride (281) (McManus, J. M. et al., J. Med. Chem. 1965, 8, 766-776) (3.80 g, 25.0 mmol) and aqueous glycolonitrile (55%, 2.7 mL, 27.6 mmol), and the resulting solution stirred at 70° C. for 1.5 h. The solution was cooled to 20° C. and diluted with water (40 mL). The aqueous layer was extracted with Et2O (4×50 mL), the combined organic fraction dried and the solvent evaporated to give nitrile 282 (3.76 g, 97%) as a colourless oil, which was used without further purification: 1H NMR δ 3.54 (s, 2H, CH2CN), 3.36-3.40 (m, 1H, H-3), 3.37 (s, 3H, OCH3), 2.77 (dd, J=10.9, 3.2 Hz, 1H, H-2), 2.44-2.56 (m, 3H, H-2, H-6), 1.75-1.85 (m, 2H, H-4, H-5), 1.52-1.57 (m, 2H, H-4, H-5).

Provenance & Evidence