Hydroxyacetonitrile → 2-(3-Methoxyazetidin-1-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-methoxyazetidine hydrochloride (275) (MacKenzie et al., PCT Int Appl. WO 9605193, 1996) (3.0 g, 24.4 mmol), aqueous glycolonitrile (55%, 3.4 mL, 34.3 mmol) and Et3N (5.2 mL, 37.3 mmol) was stirred at 20° C. for 3 h, then heated at 50° C. for 1 h. The solution was cooled and partitioned between water (50 mL) and Et2O (50 mL). The organic fraction was washed with water (2×50 mL) and brine (50 mL), dried and the solvent evaporated to give nitrile 276 (1.76 g, 57%) as a colourless oil: 1H NMR δ 4.06 (p, J=5.7 Hz, 1H, CHO), 3.61-3.66 (m, 2H, CH2N), 3.49 (s, 2H, CH2CN), 3.28 (s, 3H, OCH3), 3.22-3.27 (m, 2H, CH2N); MS (APCI) m/z 127 (MH+, 100%).

Provenance & Evidence