tert-Butyldimethylsilyl chloride → HCID 54390314, compound

To a stirred solution of 10.00 g (44.1 mmol) of the product of Step A in 100 mL methylene chloride was added 6.468 g (52,9 mmol) of 4-dimethyl-aminopyridine, 7.980 g (52.9 mmol) of tert-butyldimethylchlorosilane and the mixture was stirred at room temperature for 3 hours. The reaction mixture was partitioned between methylene chloride and water, the organic layer was separated washed with 1.0N HCl, 5% NaHCO3, dried (MgSO4), filtered and evaporated. The residue was dissolved in 35 mL of anhydous THF, magnetically stirred at 0° C., and then treated with 100 mL of a 1.0M solution of lithium triethylborohydride under a nitrogen atmosphere. The reaction was allowed to warm to room temperature, and treated with several mL water until hydrogen evolution ceased. The reaction mixture was evaporated in vacuo, redissolved in methylene chloride, dried (MgSO4), filtered and reevaporated in vacuo. The residue was finally redisolved in 30 mL THF and treated with 45 mL of a 1.0M solution of tetrabutylammonium fluoride in THF while stirring for 12 hours at room temperature. The reaction mixture was then evaporated to an oil and purified on a silica gel flash chromatography column eluted with methylene chloride to afford 4.992 g (57%) of the title compound.

1. customThe reaction mixture was partitioned between methylene chloride and water
2. customthe organic layer was separated
3. washwashed with 1.0N HCl, 5% NaHCO3
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. dissolutionThe residue was dissolved in 35 mL of anhydous THF
8. stirringmagnetically stirred at 0° C.
9. additiontreated with 100 mL of a 1.0M solution of lithium triethylborohydride under a nitrogen atmosphere
10. temperatureto warm to room temperature
11. additiontreated with several mL water until hydrogen evolution
12. customThe reaction mixture was evaporated in vacuo
13. dissolutionredissolved in methylene chloride
14. dry with materialdried (MgSO4)
15. filtrationfiltered
16. customreevaporated in vacuo
17. additiontreated with 45 mL of a 1.0M solution of tetrabutylammonium fluoride in THF
18. stirringwhile stirring for 12 hours at room temperature
19. customThe reaction mixture was then evaporated to an oil
20. custompurified on a silica gel flash chromatography column
21. washeluted with methylene chloride

ORD record

ord-021180d75b6144ee95071cc45c0e13cc

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374638