AI Article Synopsis
- The compound (1R,5S)-2-Methyl-6,7-benzomorphan was synthesized starting from (R)-(benzyloxy)(phenyl)acetaldehyde using a series of chemical reactions.
- The synthesis involved a Bi (OTf) promoted Aza-Prins reaction resulting in an 88/12 mixture of diastereoisomers, with the major one converted to an enantiomerically pure piperidin-4-ol.
- Finally, the piperidinol underwent an acid-catalyzed intramolecular Friedel-Crafts cyclization, leading to the desired benzomorphan product through a five-step process with a total yield of 25%.
Article Abstract
(1R,5S)-2-Methyl-6,7-benzomorphan has been synthesised from (R)-(benzyloxy)(phenyl)acetaldehyde. On a 2-mmol scale Bi (OTf) promoted Aza-Prins reaction with N-tosylhomoallylamine afforded an 88/12 mixture of 6-oxa-2-azabicyclo[3.2.1]octanes. Major diastereoisomer was converted to enantiomerically pure (2S,4S)-2-benzyl-1- methylpiperidin-4-ol via a high-yielding sequence hydrogenolysis/N-detosylation/N-methylation. Acid-catalysed intramolecular Friedel-Crafts cyclisation of the piperidinol afforded (1R,5S)-2-methyl-6,7-benzomorphan in five steps with a yield of 25%.
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| http://dx.doi.org/10.1002/chir.23338 | DOI Listing |
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