cis-3-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]cyclobutaneMethanol synthesis

Yield: 92%

Reaction Conditions:

with hydrogen;palladium on activated charcoal in ethanol at 20; under 760.051 Torr; for 72 h;

Steps:

16.D (cis-3-(tert-butyldimethylsilyloxy)cyclobutyl)methanol
Example 16D (cis-3-(tert-butyldimethylsilyloxy)cyclobutyl)methanol A solution of the product of Example 16C (1.15 g, 3.8 mmol) in ethanol (20 mL) was degassed three times with a N₂ back-flush each time. Palladium on carbon (0.080 g, 0.75 mmol) was added and the mixture was degassed three times with an N₂ back-flush each time. The system was put under 1 atm of H₂ (balloon) and was allowed to stir at ambient temperature for 72 h at which time the mixture was degassed three times with a N₂ backflush each time. The mixture was filtered through Celite, concentrated under reduced pressure and purified via column chromatography (SiO₂, 50% hexanes/EtOAc) to give the title product (0.75 g, 3.5 mmol, 92% yield). MS (DCI/NH₃) m/z 217 (M+H)⁺.

References:

ABBOTT LABORATORIES US2009/105306, 2009, A1 Location in patent:Page/Page column 31