Reductive cleavage of phosphinanilides with lithium aluminum hydride

1974 ◽  
Vol 39 (15) ◽  
pp. 2296-2298 ◽  
Author(s):  
Paul D. Henson ◽  
Steven B. Ockrymiek ◽  
Raymond E. Markham
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Reductive Cleavage ◽  
Lithium Aluminum

THE SYNTHESIS OF SOME INDOLYLALKYLAMINOALCOHOLS

1960 ◽  
Vol 38 (9) ◽  
pp. 1434-1438 ◽  
Author(s):  
Gerassimos Frangatos ◽  
Geza Kohan ◽  
Francis L. Chubb
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Reductive Cleavage ◽  
Lithium Aluminum ◽  
Carbonyl Groups ◽  
Open Chain ◽  
Hydride Reduction

A series of 3-indolylalkylaminoalcohols have been obtained from the lithium aluminum hydride reduction of the amides prepared by the reaction of 3-indoleglyoxylyl chloride and 2-methyl-3-indoleglyoxylyl chloride with primary aminoalcohols. When acetone was used as solvent in the reaction of 3-indoleglyoxylyis chloride and either 2-aminoethanol or 3-aminopropanol, the solvent participated in the reaction resulting in the formation of 2,2-dimethyl-3-(3-indoleglyoxyl)oxazolidine and 2,2-dimethyl-3-(3-indoleglyoxyl)tetrahydro-1,3-oxazine respectively. When the latter two compounds were reduced by lithium aluminum hydride, both carbonyl groups were completely reduced and reductive cleavage of the oxazolidine and tetrahydro-1,3-oxazine rings occurred to form the corresponding open-chain alcohols.

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