Methods for the preparation of (3r,3as,6ar)...

Details Methods for the preparation of (3r,3as,6ar)... Methods for the preparation of (3r,3as,6ar)...

C - Chemistry, Metallurgy

07

D

C07D 493/04 (2006.01) C07D 307/20 (2006.01) C07H 15/04 (2006.01)

Patent

CA 2559959

The present invention relates to methods for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol (6) as well as a novel intermediate, (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4- b]furan-2-one (4) for use in said methods. More in particular the invention relates to a stereoselective method for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol, as well as methods for the crystallization of (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan- 2-one and for the epimerization of (3aR,4R,6aS) 4-methoxy-tetrahydro-furo[3,4-b]- furan-2-one to (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one.

Cette invention concerne des procédés de préparation de (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol (6) diastéréomériquement pur ainsi qu'un nouvel intermédiaire, le (3aR,4S,6aS) 4-méthoxy-tétrahydro-furo[3,4-b]furan-2-one (4), utilisé dans ces procédés. Cette invention concerne plus particulièrement un procédé stéréosélectif de préparation de (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol (6) diastéréomériquement pur, ainsi que des procédés de cristallisation de (3aR,4S,6aS) 4-méthoxy-tétrahydro-furo[3,4-b]furan- 2-one et d'épimérisation de (3aR,4R,6aS) 4-méthoxy-tétrahydro-furo[3,4-b]-furan-2-one en (3aR,4S,6aS) 4-méthoxy-tétrahydro-furo[3,4-b]furan-2-one.

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