Dimethyl Sulfide → HCID 23291907, compound

Temperature

0 °C

7-Bromo-1-isopropyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 31, 12.46 g, 42.08 mmol) was dissolved in toluene (100 mL) and the solution was cooled to 0° C. and treated with 2.0 M of BH3.SMe2 (23.14 mL, 46.28 mmol) in THF. The solution was stirred at 0° C. for 1 hour and at room temperature overnight, and the reaction mixture was treated with 10% aqueous Na2CO3. The solution was stirred at room temperature for 1 hour, the layers were separated and the aqueous layer extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (2% ethyl acetate in hexane, Rf=0.31) to give the title compounds (11.28 g, 95% over 3 steps) as an oil:

1. additiontreated with 2.0 M of BH3
2. stirringThe solution was stirred at room temperature for 1 hour
3. customthe layers were separated
4. extractionthe aqueous layer extracted twice with ethyl acetate
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel chromatography (2% ethyl acetate in hexane, Rf=0.31)

ORD record

ord-8e5ffc586c174e31b2404ef4f8593c4f

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127382