Hydroxyacetonitrile → 3-Methoxy-1-azetidineacetonitrile

Temperature

50 °C

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%).

1. temperatureThe solution was cooled
2. custompartitioned between water (50 mL) and Et2O (50 mL)
3. washThe organic fraction was washed with water (2×50 mL) and brine (50 mL)
4. customdried
5. customthe solvent evaporated

ORD record

ord-8e31792a85fb40eaa0553ed2b8be403b

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2