Benzyl Bromide → HCID 9911651, compound

Temperature

-78 °C

A solution of 0.228 g (0.63 mmol) of the product of Example 1 was dissolved in 0.5 mL of anhydrous THF in an oven dried 25 mL round bottom flask and was magnetically stirred at -78° C. under a nitrogen atmosphere. A solution of lithium bis(trimethylsilyl)amide (1.89 mL; 1.0M; 1.89 mmol) was slowly added and the resulting yellow solution was stirred at -78° C. for 1 hour. At this point 150 μL (1.26 mmol) of benzyl bromide was added via syringe, the dry ice-acetone bath was removed, the reaction mixture was allowed to warm to room temperature and was stirred an additional 2 hours. The mixture was then partitioned between EtOAc and 10% aqueous NaHSO4 and extracted. The organic layer was separated, washed once with water, once with saturated brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH--NH4OH (92:8:0.5). Evaporation of the purified fractions and drying in vacuo afforded 0.183 g (64%) of the title compound.

1. customdried 25 mL round bottom flask
2. stirringthe resulting yellow solution was stirred at -78° C. for 1 hour
3. customthe dry ice-acetone bath was removed
4. temperatureto warm to room temperature
5. stirringwas stirred an additional 2 hours
6. customThe mixture was then partitioned between EtOAc and 10% aqueous NaHSO4
7. extractionextracted
8. customThe organic layer was separated
9. washwashed once with water, once with saturated brine
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customevaporated
13. customThe residue was purified on a silica gel flash chromatography column
14. washeluted with CHCl3 -MeOH
15. customEvaporation of the purified fractions
16. customdrying in vacuo

ORD record

ord-35e81ad12fd24ed8a5c1f449dfbeb689

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686478