Hydrogen Peroxide → 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine oxide hydrate

30% Aqueous H2O2 (18 mL) was added dropwise to a stirred solution of 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine (12 g, 80 mmol) prepared in Part B in methanol (100 mL) at 5 to 22° C. over 2 h. After stirring at RT for 20 h, additional 30% H2O2 (18 mL) was added. After 3 h, Pd black slurry (150 mg) in water (3 mL) was added to the stirred reaction mixture in small portions such that the temperature could be maintained between 5 to 25° C. with a cooling bath. The reaction mixture was stirred at RT for 1 h until the O2 evolution ceased. After filtration, the filtrate was concentrated in vacuo to give 1-(3,3-difluorocyclobutyl)-N,N-dimethylmethanamine oxide hydrate as a thick colorless oil (15 g, semisolid). 1H NMR (400 MHz, CD3OD) δ ppm 3.47 (2H, d, J=5.29 Hz), 3.16 (6H, s), 2.75-2.92 (3H, m), 2.42-2.58 (2H, m).

1. waitAfter 3 h
2. temperaturecould be maintained between 5 to 25° C. with a cooling bath
3. filtrationAfter filtration
4. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-c9c4d2c9eb8f470b882a0f5e06c21da6

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580959B2