Reductive One Batch Synthesis of N-Substituted Pyrrolidines from Primary Amines and 2,5-Dimethoxytetrahydrofuran

Giancarlo Verardo; Anna Dolce; Nicoletta Toniutti

doi:10.1055/s-1999-3685

Synthesis 1999; 1999(1): 74-79
DOI: 10.1055/s-1999-3685

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Reductive One Batch Synthesis of N-Substituted Pyrrolidines from Primary Amines and 2,5-Dimethoxytetrahydrofuran

Giancarlo Verardo^* , Anna Dolce, Nicoletta Toniutti

^*Department of Chemical Sciences and Technologies, University of Udine, I-33100 Udine, Italy; Fax +0 39(04 32)55 88 03; E-mail: gverardo@tin.dstc.uniud.it

Abstract

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The construction of the pyrrolidine ring about a nitrogen of a primary amine by a reductive condensation reaction using 2,5-dimethoxytetrahydrofuran and sodium borohydride in acidic water medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electron effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups. The reaction allows the introduction of two deuterium atoms, with label conservation, in both the α-positions of the pyrrolidine ring by the use of sodium borodeuteride instead of sodium borohydride.

pyrrolidine - 2,5-dimethoxytetrahydrofuran - sodium borohydride - sodium borodeuteride - reductive alkylation

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