Hydrogen Peroxide → HCID 25242003, compound

Sodium borohydride (0.235 mg) was suspended in tetrahydrofuran (2.0 mL) in an argon flow, and the suspension was cooled with ice. Optically active α-pinene (0.63 mL) and boron trifluoride.ether complex (0.25 mL) were added dropwise to the suspension, and the mixture was stirred for 12 hours. 1-Diphenylmethyl-3-pyrroline (0.24 g) was added to the reaction mixture, and the resultant mixture was allowed to react for 9 hours. Thereafter, 30% aqueous hydrogen peroxide (2 mL) and 6 mol/L aqueous sodium hydroxide (2 mL) were added dropwise to the reaction mixture. After 3 h, the reaction mixture was extracted with methylene chloride, and the formed organic layer was dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystalline residue. The residue was subjected to silica gel chromatography, to thereby give the target compound (0.200 g, yield 79%). HPLC analysis (through use of a Daicel Chiral Pack AD-RH) of the thus-obtained compound indicates that the compound has an optical purity of 72% ee.

1. temperaturethe suspension was cooled with ice
2. additionether complex (0.25 mL) were added dropwise to the suspension
3. customto react for 9 hours
4. waitAfter 3 h
5. extractionthe reaction mixture was extracted with methylene chloride
6. dry with materialthe formed organic layer was dried over sodium sulfate
7. customThe drying agent was removed through filtration
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-431efa41fe494b2680068ecb0433c734

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994344B2