(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

Uses

(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol was used to preapare AZD6140 as an orally active reversible P2Y12 receptor antagonist for prevention of thrombosis.

Synthesis

0.86 g of p-toluenesulfonic acid was added to a solution of 15.0 g of the precursor compound in acetone ( 250 ml ) followed by 22 ml of 2,2 -dimethoxypropane, and the resulting reaction mixture was stirred at room temperature for 30 minutes. At the end of the reaction the mixture was separated by extraction between ethyl acetate ( 700 ml ) and brine ( 300 ml ), the organic layer was separated and concentrated, water was added to the residue, which was heated and refluxed for 24 h. At the end of the reaction the reaction solution was concentrated under reduced pressure and azeotropized with toluene to remove water to give (3AR,4S,6R,6AS)-6-aminotetrahydro-2,2-dimethyl-4H- cyclopenteno-1,3-dioxolan-4-ol.