Ammonium Chloride → 5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanol

Sodium bis(trimethylsilyl)amide (76.27 mL, 1 M in tetrahydrofuran, 76.27 mmol) was added drop wise to a stirred and cooled (0° C.) solution of cyclooctane-1,5-diol (10 g, 69.34 mmol) in dry tetrahydrofuran (120 mL). After the addition, the resulting solution was warmed to room temperature and stirred for another thirty minutes. The solution was re-cooled (0° C.) and a solution of tert-butyl-chloro-dimethyl-silane (10.45 g, 69.34 mmol) in tetrahydrofuran (20 mL) was added drop wise. The solution was then warmed to room temperature and stirred overnight before an NH4Cl solution was added. The mixture was partitioned with diethyl ether, and the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 2-40% ethyl acetate in hexanes to provide the title compound as an oil.

1. additionAfter the addition
2. stirringstirred for another thirty minutes
3. temperatureThe solution was re-cooled (0° C.)
4. temperatureThe solution was then warmed to room temperature
5. additionwas added
6. customThe mixture was partitioned with diethyl ether
7. washthe organic phase was washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified over silica gel using 2-40% ethyl acetate in hexanes

ORD record

ord-4ff8a344caee4ac3a8cd84336c098d8c

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737137B2