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Paper | Regular issue | Vol 31, No. 11, 1990, pp.2079-2084
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5574
Some Observations on the Regioselective Ring Opening of Tetrahydro-1,3-oxazinium Methiodides by Sodium Borohydride in Alcholic and Etheral Solvents

Angel Alberola, Celia Andrés, Manuel Delgado, Alfonso González, and Rafael Pedrosa*

*Deparamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid, Spain

Abstract

2-Substituted N-benzyl-N-methyltetrahydro-1,3-oxazinium iodides react with sodium borohydride in anhydrous THF leading to a mixture of 3-alkoxypropylamines and their borane complexed. On the contrary, when anhydrous methanol or ethanol is used as solvent, the corresponding transacetalization product is obtained as single compound.