Tetrahedron Letters

Application of Grignard reagents to the synthesis of tertiary methylamines via resin-bound oxyiminium ions

P Blaney, R Grigg, Z Rankovic, M Thoroughgood

Index: Blaney; Grigg; Rankovic; Thoroughgood Tetrahedron Letters, 2000 , vol. 41, # 34 p. 6639 - 6642

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Citation Number: 19

Abstract

The solid-phase synthesis of tertiary methylamines via the nucleophilic displacement of benzotriazole Mannich adducts with Grignard reagents using a hydroxylamine linker is described. The chemistry is exemplified by the synthesis of the MAO inhibitor α- methylpargyline. Also described is the synthesis of the analgesic Tramadol by an alternative one-pot solid-phase Mannich reaction.