Hydrogen Peroxide → HCID 67490784, compound

A solution of a borane-tetrahydrofuran complex in tetrahydrofuran (1 M, 187 mL, 187 mmol) was added dropwise to a solution of 2-(tritylamino)methyl-5,6-dihydro-4H-pyran (22.2 g, 62.4 mmol) in tetrahydrofuran (180 mL) at room temperature over 20 minutes. After stirring at room temperature for 2.5 hours, the reaction solution was ice-cooled, and a 3N sodium hydroxide solution (208 mL, 624 mmol) was added dropwise over 10 minutes. Subsequently a 31% hydrogen peroxide solution (69 mL, 629 mmol) was added dropwise at the same temperature over 10 minutes, and then the mixture was stirred at room temperature for one hour. The reaction solution was extracted with diethyl ether (2×300 mL). The combined organic layers were washed with water (300 mL) and brine (300 mL), and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and then the residue was suspended in a mixed solvent of dichloromethane/hexane (1:1, 80 mL). The insoluble material was removed by filtration, and then the filtrate was evaporated under reduced pressure to give 18.54 g (80%) of the title compound as a pale yellow gummy solid.

1. temperaturecooled
2. stirringthe mixture was stirred at room temperature for one hour
3. extractionThe reaction solution was extracted with diethyl ether (2×300 mL)
4. washThe combined organic layers were washed with water (300 mL) and brine (300 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customThe solvent was evaporated under reduced pressure
8. customThe insoluble material was removed by filtration
9. customthe filtrate was evaporated under reduced pressure

ORD record

ord-4993549538ac41a8994885d702c6b155

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2