Reduction of some N-alkyl- and N-aryl-pyrrolidin-2-ones and -piperidin-2-ones by lithium aluminium hydride
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 885-891
- https://doi.org/10.1039/p19740000885
Abstract
Reduction of 1-methyl-pyrrolidin-2-one (1) and -piperidin-2-one (9) by lithium aluminium hydride (0·25 mol. equiv.) yielded 1-methyl-3-(1-methylpyrrolidin-2-yl)-Δ2-pyrroline (7) and 1,2,3,4-tetrahydro-1-methyl-5-(1-methylpiperidin-2-yl)pyridine (14), respectively. Similar reduction of 3,3-dimethyl-1-p-tolylpyrrolidin-2-one afforded 3,3-dimethyl-1-p-tolylpyrrolidin-2-ol (15); but 1-p-tolylpyrrolidin-2-one and 3-methyl-1-p-tolylpyrrolidin-2-one gave 2,3,3a,3b,4,5,6,11b-octahydro-10-methyl-1-p-tolyl-1H-dipyrrolo[1,2-a:3′,2′-c]quinoline (19; R = Me) and 2,3,3a,3b,4,5,6,11b-octahydro-3a,4,10-trimethyl-1-p-tolyl-1H-dipyrrolo[1,2-a:3′,2′-c]quinoline (25), respectively, each being obtained in two stereoisoeric forms. In the case of 1-p-tolylpiperidin-2-one it was possible to isolate 1,2,3,4-tetrahydro-1-p-tolylpyridine (30; R = Me).Keywords
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