Journal
MOLECULES
Volume 26, Issue 19, Pages -Publisher
MDPI
DOI: 10.3390/molecules26196000
Keywords
appel reaction; alkylation; nitroxide; azepane; Hofmann elimination
Funding
- RFBR [ST2017-382, 18-53-76003-ERA-A]
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The activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to synthesize various functional derivatives. The reactions of specific compounds with MsCl/NR3 or PPh3-CBr4 led to the formation of different derivatives depending on the substituent X. Subsequent alkylation and Hofmann elimination of one derivative resulted in a specific compound with 56% yield.
Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh3-CBr4 system is a commonly used pathway to various functional derivatives. The reactions of (5R(S),6R(S))-1-X-6-(hydroxymethyl)-2,2-dimethyl- 1-azaspiro[4.4]nonanes 1a-d (X = O center dot; H; OBn, OBz) with MsCl/NR3 or PPh3-CBr4 were studied. Depending on substituent X, the reaction afforded hexahydro-1H,6H-cyclopenta[c]pyrrolo[1,2-b]isoxazole (2) (for X = O), a mixture of 2 and octahydrocyclopenta[c]azepines (4-6) (for X = OBn, OBz), or perhydro-cyclopenta[2,3]azeto[1,2-a]pyrrol (3) (for X = H) derivatives. Alkylation of the latter with MeI with subsequent Hofmann elimination afforded 2,3,3-trimethyl-1,2,3,4,5,7,8,8a-octahydrocyclopenta[c]azepine with 56% yield.
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