bicyclo[2.2.2]octane-1-carboxylicacid

A flask was charged with 4-(methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid (1 g, 4.71 mmol), 2, 2'-disulfanediylbis(pyridine 1-oxide) (1.427 g, 5.65 mmol), and dichloromethane (50 mL). The flask was masked with foil to reduce ambient light. The resulting suspension was cooled to 0 °C and treated with tributylphosphine (1.453 mL, 5.89 mmol) drop wise. The ice bath was removed and stirring continued for 2 h. The reaction was cooled to 0 °C and treated with 2-methylpropane-2 -thiol (4.7 mL, 41.7 mmol). The reaction was irradiated with a 300W Tungsten lamp for 1.25 h. The reaction was quenched by addition of a suspension of 10 g calcium hypochlorite in water (100 mL). The mixture was diluted with ether and stirred at 0 °C for 5 min, followed by room temperature for 20 min. Celite was added to aid in separation of the layers, and the resulting mixture filtered. The eluent was poured into a separatory funnel and the layers separated. The organics were washed with brine, dried over magnesium sulfate, and concentrated. The resulting residue was treated with a solution of 5 g potassium hydroxide in 100 mL methanol/water (1 :1). The resulting mixture was stirred at room temperature over the weekend. The reaction was concentrated to remove most of the methanol and extracted with ether (2X) to remove byproducts (discarded). The aqueous was made acidic by addition of concentrated HC1 upon which a white precipitate was formed. The precipitate was collected by filtration to afford 530 mg (66percent).

Molecular Weight:154.21
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:154.099379685
Monoisotopic Mass:154.099379685
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes