Method for the enantiomer separation of cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane

• Main Author: Fey, Peter
• Format: Patent
• Language: English
• Published: 20.05.2003

The present invention relates to a process for the separation of enantiomers of cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane (also called cis-6-benzyl-5,7-dioxooctahydropyrrolo[3,4-b]pyridine or dioxopyrrolopiperidine below). In a further aspect, the invention relates to a process for the preparation of (1S,6R)- and ( R,6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane using the aforementioned process. The invention furthermore relates to the (−)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid salts of (1S,6R)- and (1R,6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane, and to a process for their preparation. The invention further relates to a process for the enrichment of enantiomers of (1S,6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane. The invention relates to a method for the enantiomer separation of cis-8-benzyl-7,9-dioxo-2,8-diazabicy-clo[4.3.0]nonane (also described below as cis-6-benzyl-5,7-dioxooctahydropyrrolo[3,4-b]pyridine or dioxopyrrolopiperidine). The invention also relates to a method for producing (1S, 6R)- and (1R, 6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane using the above method. The invention further relates to the (−)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid salts of (1S, 6R)- and (1R, 6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane and to a method for producing the same. Finally, the invention relate to a method for the enantiomer enrichment of (1S, 6R)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]-nonane.