Borane → (3-Aminoadamantan-1-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 5.98 g of 3-amino-1-adamantanecarboxylic acid in 40 ml of dry tetrahydrofuran stirred under a nitrogen atmosphere is added 6.5 ml of boron trifluoride etherate. Stirring is continued as 35 ml of a 1 M solution of borane in tetrahydrofuran is added at a rate which maintains reflux. The reaction mixture is refluxed for 4.5 hours then cooled and 20 ml of a 4 N solution of sodium hydroxide is added dropwise. The upper phase, which contains the tetrahydrofuran and the borate ester of the product, is separated. The tetrahydrofuran is removed under reduced pressure, and the residue is heated with 40 ml of a 4 N sodium hydroxide solution for 24 hours at 100° C. The solution is extracted three times with 200 ml of chloroform. The combined chloroform extracts are dried over potassium carbonate and the solvent is removed under reduced pressure. The residue is stirred with diethyl ether to give a crystalline product, 3-amino-1-adamantanemethanol which is represented by the following structure ##STR69##

Provenance & Evidence