4-Azatricyclo[4.3.1.13,8]undecan-5-one → 4-Azatricyclo[4.3.1.13,8]undecane

Participants

Reaction Steps

To a solution of diborane in tetrahydrofuran (1M, 20 ml) was added dropwise a solution of 2-azatricyclo[4.3.1.14,8 ]-undecan-3-one (1.01 g) in dry tetrahydrofuran (20 ml) under stirring at cooling in an ice-bath. The mixture was stirred under the same condition for 2 hours and then at room temperature overnight. To the reaction mixture was added dropwise IN hydrochloric acid aqueous solution (20 ml). After removal of the solvent under reduced pressure, the residue was washed with ethyl acetate. The aqueous layer was alkalined with IN sodium hydroxide aqueous solution, extracted with ethyl acetate three times and dried over sodium sulfate. Removal of the solvent gave 2-azatricyclo[4.3.1.14,8 ]undecane (0.48 g), which was used in a following reaction step without further purification.

Provenance & Evidence