Water → 8-Benzyl-8-azabicyclo[3.2.1]octan-3-ol

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Reaction Steps

In tetrahydrofuran (16 ml) was dissolved 8-benzyl-8-azabicyclo[3.2.1]octan-3-one (1.0 g, 4.64 mmol), and a 1M-diisobutylaluminum hydride/toluene solution (11.6 ml, 11.6 mmol) was added dropwise thereto at −78° C. over a period of 10 minutes and stirred for another 1 hour. Water was added dropwise thereto to quench the excess reactants, and the resulting mixture was separated by the addition of a 2N-aqueous hydrochloric acid solution and ethyl acetate. The aqueous layer was adjusted to pH 10 or lower with a 2N-aqueous sodium hydroxide solution and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain 8-benzyl-8-azabicyclo[3.2.1]octan-3-ol (886 mg, 88%).

Provenance & Evidence