Preparation of (1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl...

C - Chemistry – Metallurgy – 07 – C

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C07C 49/297 (2006.01) C07C 29/40 (2006.01) C07C 35/18 (2006.01) C07C 43/188 (2006.01) C07C 45/58 (2006.01) C07C 45/67 (2006.01) C07C 49/337 (2006.01) C07C 69/03 (2006.01) C07C 69/78 (2006.01) C07C 69/96 (2006.01) C07D 303/14 (2006.01) C07D 303/16 (2006.01) C07D 303/22 (2006.01) C07D 303/31 (2006.01) C07D 309/12 (2006.01) C07D 407/12 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2143992

A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia Image Image (I), (Ia) which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the gen- eral formula II Image (II), where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI Image Image (V) (VI), by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII Image (VIII) (R=H or protective group) with Lewis acids and, where appropriate, removal of the protec- tive group. Also claimed are the novel intermediates of the for- mula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.

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