Acetone → HCID 59104136, compound

Temperature

-78 °C

2.76 g (9.9 mmol) (R)-diallyl-[1-(4-bromo-phenyl)-ethyl]-amine was dissolved in 30 ml THF (dry) under N2 atmosphere. The mixture was then cooled to −78° C. and 5.0 ml (12 mmol) of 2.5M n-BuLi in hexanes was added drop-wise. The mixture was then cooled to −90° C. and acetone was added, while stirring continued at −90° C. for 10 m. The mixture was then allowed to warm to room temperature and the reaction was thereafter quenched with MeOH. Water was then added and the resulting mixture was extracted with ether. The ether extracts were combined; washed with water and brine; dried over MgSO4; and filtered and concentrated in vacuo. Chromatography on silica gel using 15% ethyl acetate/hexanes yielded 1.6 g (64%) of the desired final product.

1. temperatureThe mixture was then cooled to −90° C.
2. customcontinued at −90° C. for 10 m
3. temperatureto warm to room temperature
4. customthe reaction was thereafter quenched with MeOH
5. additionWater was then added
6. extractionthe resulting mixture was extracted with ether
7. washwashed with water and brine
8. dry with materialdried over MgSO4
9. filtrationand filtered
10. concentrationconcentrated in vacuo

ORD record

ord-30889150bddb47a68b3202f6eaae551b

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354941B2