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Author: Subject: N-Boc-7-Azanorborn-2-one [152533-47-6]
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[*] posted on 21-3-2021 at 06:23
N-Boc-7-Azanorborn-2-one [152533-47-6]


Does anybody know if N-Boc-pyrrole can react with ketene in a single step to give the title compound?

I think actually you have to catalytically hydrogenate the olefin bond.

I know in the lab it was made using a different procedure, then it becomes like a slave labour than trivially easy to do.


[Edited on 21-3-2021 by Illegal Parkinson]
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[*] posted on 21-3-2021 at 22:15


xfiles.gif - 5kB
Okay, recently I figured that a double Michael addition of methylamine to 2,6-cycloheptadienone [1192-93-4]

https://en.wikipedia.org/wiki/Tropinone#From_cycloheptanone

So i figure if i shrink to six memebered ring get cyclohexa-2,5-dienone.

6-Methyl-6-aza-bicyclo[3.1.1]heptan-3-one
https://pubchem.ncbi.nlm.nih.gov/compound/23542376

So, i figure, this is the wrong isomer, i need keto-enol tautomer of phenol.

2,4-Cyclohexadienone
https://pubchem.ncbi.nlm.nih.gov/compound/141125
[24599-57-3] so-called "benzene one"

However, only one of the olefins can partake in a conjugate addition.

This is the so-called [4 + 1] Cycloaddition

Alternatively, another option is the unconjugated olefin could be replaced by a leaving group such as bromide or tosylate?

[Edited on 22-3-2021 by Illegal Parkinson]
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[*] posted on 21-3-2021 at 23:46


Maybe if an amine cannot add to the diene, maybe a nitrene could work?

So conceptually if have phenol in the keto tautomer,

a 4 + 1 addition can work?
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[*] posted on 27-3-2021 at 05:39


Okay, i thought to myself if phenol-ketone can be trapped as the acetal

this concenptually might work,

for example, tke cyclic acetal is called 1,4-dioxaspiro[4.5]deca-6,8-diene [23783-59-7].
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