Feretile
Bluelighter
- Joined
- Feb 2, 2022
- Messages
- 361
I have a reference the German language patent concerning the synthesis of fencamfamine ((1S,4R)-N-Ethyl-3-phenylbicyclo[2.2.1]heptan-2-amine).I am trying to divine if the synthesis uses:
a)[ (Z)-2-nitroethenyl]benzene
b)[ (E)-2-nitroethenyl]benzene
I suspect, given the structure of fencamfamine that the latter is used. I have spent several hours searching but to no avail. It's a lovely example of a Diels-Alder condensation, possibly the simplest one. I occasionally give lectures on organic chemistry and would like to use this example. Normally I would simply draw the structure in ChemOffice, export it to Reaxys and find the English-language patent but Reaxys is off-line at the moment. DE patent 1110159 is the given reference but I KNOW I have seen a GB or US patent, but I cannot put my hand on it.
In fact, I am not trying to make fencamfamine, I intend to substitute (2Z)-3-Nitro-2-phenylacrylonitrile which will, I believe, yield:
(1S,2R)-2-nitro-3,6-dihydro[1,1'-biphenyl]-1(2H)-carbonitrile
I feel confident that nobody could possibly imagine that this is a drug of any stripe nor the precursor of any drug. I was simply asked to provide an example of a Diels-Alder condensation and to give an example of it's limitations. A nitrile is one of the few moieties I could think of that I KNOW will not interfere with the reaction.
I chose this because it packs the most moieties in the smallest compound.
a)[ (Z)-2-nitroethenyl]benzene
b)[ (E)-2-nitroethenyl]benzene
I suspect, given the structure of fencamfamine that the latter is used. I have spent several hours searching but to no avail. It's a lovely example of a Diels-Alder condensation, possibly the simplest one. I occasionally give lectures on organic chemistry and would like to use this example. Normally I would simply draw the structure in ChemOffice, export it to Reaxys and find the English-language patent but Reaxys is off-line at the moment. DE patent 1110159 is the given reference but I KNOW I have seen a GB or US patent, but I cannot put my hand on it.
In fact, I am not trying to make fencamfamine, I intend to substitute (2Z)-3-Nitro-2-phenylacrylonitrile which will, I believe, yield:
(1S,2R)-2-nitro-3,6-dihydro[1,1'-biphenyl]-1(2H)-carbonitrile
I feel confident that nobody could possibly imagine that this is a drug of any stripe nor the precursor of any drug. I was simply asked to provide an example of a Diels-Alder condensation and to give an example of it's limitations. A nitrile is one of the few moieties I could think of that I KNOW will not interfere with the reaction.
I chose this because it packs the most moieties in the smallest compound.