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filingDate 1999-12-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2011-10-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 2011-10-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber JP-4800482-B2
titleOfInvention (2S, 4R, 9S) -Octahydro-1H-indole-2-carboxylic acid production method and intermediates thereof
abstract Described is a process for the preparation of (2S, 4R, 9S)-octahydro-1H-indole-2-carboxylic acid, comprisinga) reacting a compound of the formula I wherein R1 and R2 may be the same or different and represent each a C1-4-alkyl group, with water in the presence of an acidic catalyst,b) subjecting the obtained 3,3-dialkoxypropionaldehyde of formula II to a Henry-reaction with nitromethane,c) subjecting the obtained 4,4-dialkoxy-1-nitro-4-butanol of formula III to a dehydrationd) converting the obtained nitroolefin IV with the aid of a Diels-Alder reaction into the corresponding trans-4-(2,2-dialkoxyethyl)-5-nitro-1-caclohexene Ve) hydrogenating the obtained substance V into the corresponding trans-4-(2,2-dialkoxyethyl)-5-amino-1-cyclohexane VIf) subjecting the compound VI to a resolution of racemate and obtaining the (1S, 2R)-1-amino-2-(2,2-dialkoxyethyl)-cyclohexane VII in enantiomerically pure form by enzymatic racemate resolution,g) hydrolysing the obtained compound VII to the corresponding aldehyde VIIIh) converting the obtained aldehyde into the corresponding nitrite IX by reaction with cyanide ions andi) saponifying this nitrile to the (2S, 4R, 9S)-octahydro-1H-indole-2-carboxylic acid.
priorityDate 1999-01-07-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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