The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh3-CBr4

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·; H; OBn...

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Bibliographic Details
Published in:	Molecules (Basel, Switzerland) Switzerland), 2021-10, Vol.26 (19), p.6000
Main Authors:	Khoroshunova, Yulia V., Morozov, Denis A., Taratayko, Andrey I., Dobrynin, Sergey A., Eltsov, Ilia V., Rybalova, Tatyana V., Sotnikova, Yulia S., Polovyanenko, Dmitriy N., Asanbaeva, Nargiz B., Kirilyuk, Igor A.
Format:	Article
Language:	eng
Subjects:	Alkylation appel reaction azepane Chlorides Chromatography Hofmann elimination Hydroxyl groups nitroxide Nonanes Oxidation Substitution reactions
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Summary:	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·; 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.
ISSN:	1420-3049 1420-3049