Ethyl Acetate → (3-Chloro-4-[[(4-dipropylamino-butyl)-methyl-amino]-methyl]-phenyl)-methanol

Temperature

0 °C

The compound (526.4 mg) obtained in Example 77-3 was dissolved in THF (10 ml) and the whole was cooled to 0° C. Under a nitrogen atmosphere, a 0.94 mol/l DIBAL n-hexane solution (3 ml) was dropped to the reaction solution and the whole was stirred at room temperature for 1 hour. After having been cooled to 0° C., the reaction solution was added with ethyl acetate (10 ml) and acetone (10 ml) and the whole was stirred at room temperature for 1 hour. The reaction solution was added with a saturated aqueous sodium potassium tartrate solution (30 ml) and the whole was vigorously stirred at room temperature for 2 hours and then subjected to extraction with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the resultant was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (n-hexane/ethyl acetate), thereby obtaining the subject compound (290.8 mg) as a yellow oily substance.

1. temperatureAfter having been cooled to 0° C.
2. stirringthe whole was stirred at room temperature for 1 hour
3. stirringthe whole was vigorously stirred at room temperature for 2 hours
4. extractionsubjected to extraction with ethyl acetate
5. washThe organic layer was washed with a saturated saline solution
6. dry with materialdried with anhydrous sodium sulfate
7. filtrationAfter the drying agent was filtrated out
8. concentrationthe resultant was concentrated under reduced pressure
9. customThe resultant residue was purified through silica gel column chromatography (n-hexane/ethyl acetate)

ORD record

ord-36f81b77228740ffbc9248d95045df0f

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932281B2