Sulfuric Acid → 4-Aminoadamantan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a mixture of concentrated sulfuric acid (300 ml) and concentrated nitric acid (30 ml) cooled in an ice bath to 10° C. is added tricyclo[3.3.1.13,7 ]decan-2-amine hydrochloride (20 g; 0.107 mole) in 5 g portions over 10 minutes. This mixture is then stirred for 2 hours with cooling. The reaction mixture is poured over ice and the pH raised to pH 10-11 using 40% NaOH. This mixture is extracted with chloroform, dried over MgSO4 and evaporated to dryness to give 5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine as a solid residue (m.p. 267°-270° C.) which is used directly in step B.

Provenance & Evidence