Hydrogen Peroxide → HCID 59649298, compound

Into a clean flame dried 1 L RBF under current of N2, was put 12.86 g (34.48 mmol) of 54. To this was added 172 mL (86.2 mmol) of 9-BBN (0.5 M in THF). The reaction was stirred for 3 h. 23 mL of 30% H2O2 was then added dropwise to the reaction mixture followed by 49 mL of 15% aq. NaOH and the reaction mixture was stirred at 85° C. for 3 h. The mixture was then cooled to room temperature and THF was evaporated and the residue was diluted with H2O and extracted with EtOAc (3×). The combined organic layer was then washed with brine (1×), dried over MgSO4, filtered and the solvent was evaporated under vacuum. The residue was then purified using combiflash (120 g silica column) with hexane/ethyl acetate as eluent to furnish 10.15 g (76%) of compound 55 as a white solid.

1. temperatureInto a clean flame
2. dry with materialdried 1 L RBF under current of N2
3. stirringthe reaction mixture was stirred at 85° C. for 3 h
4. customTHF was evaporated
5. additionthe residue was diluted with H2O
6. extractionextracted with EtOAc (3×)
7. washThe combined organic layer was then washed with brine (1×)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customthe solvent was evaporated under vacuum
11. customThe residue was then purified

ORD record

ord-23a768b5a5f0445e9db8e04d8e3f4643

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749983B2