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

ABSTRACT: 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.

SUBMITTER: Khoroshunova YV 

PROVIDER: S-EPMC8512565 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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The Reactions of 6-(Hydroxymethyl)-2,2-dimethyl-1-azaspiro[4.4]nonanes with Methanesulfonyl Chloride or PPh<sub>3</sub>-CBr<sub>4</sub>.

Khoroshunova Yulia V YV   Morozov Denis A DA   Taratayko Andrey I AI   Dobrynin Sergey A SA   Eltsov Ilia V IV   Rybalova Tatyana V TV   Sotnikova Yulia S YS   Polovyanenko Dmitriy N DN   Asanbaeva Nargiz B NB   Kirilyuk Igor A IA  

Molecules (Basel, Switzerland) 20211002 19

Activation of a hydroxyl group towards nucleophilic substitution via reaction with methanesulfonyl chloride or PPh<sub>3</sub>-CBr<sub>4</sub> system is a commonly used pathway to various functional derivatives. The reactions of (5<i>R</i>(<i>S</i>),6<i>R</i>(<i>S</i>))-1-X-6-(hydroxymethyl)-2,2-dimethyl- 1-azaspiro[4.4]nonanes 1<b>a</b>-<b>d</b> (X = O·; H; OBn, OBz) with MsCl/NR<sub>3</sub> or PPh<sub>3</sub>-CBr<sub>4</sub> were studied. Depending on substituent X, the reaction afforded hexah  ...[more]

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