Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 69312848, compound

To a sample of 103 mg (0.822 mmol) of 1H,3H,4H,7H,8H-azocin-2-one in 5 mL of dichloromethane was added 183 mg (1.234 mmol) of trimethyloxonium tetrafluoroborate. The reaction was stirred at room temperature for 16 h, after which time it was diluted with 15 mL of methylene chloride and extracted twice with 5 mL of saturated aqueous NaHCO3 and once with 5 mL of brine. The organic layer was dried over MgSO4, filtered, and the concentrated under reduced pressure. The 8-methoxy-2H,3H,6H,7H-azocine thus produced (92 mg) was used without purification in the next reaction. 1H NMR (500 MHz, CDCl3): δ 5.82 (m, 1H), 5.69 (m, 1H), 4.22 (s, 3H), 4.04 (q, 2H, J=6 Hz), 3.03 (t, 2H, J=6 Hz), 2.73 (br apparent q, 2H, J=6 Hz), 2.63 (apparent q, 2H, J=6 Hz).

1. extractionextracted twice with 5 mL of saturated aqueous NaHCO3 and once with 5 mL of brine
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationthe concentrated under reduced pressure

ORD record

ord-7f3b95045b5e4893825a400ca6314291

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329683B2