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Paper | Regular issue | Vol 60, No. 5, 2003, pp.1111-1122
Published online, 17th March, 2003
DOI: 10.3987/COM-03-9713
Nucleophilic Reactions at Optically Active Bis(4-methyl-5-phenyl-1,3-oxazolidin-3-yl)methane

Raúl Salas-Coronado, Sonia A. Sánchez-Ruiz, Juan Carlos Gálvez-Ruiz, and Angelina Flores-Parra*

*Department of Chemistry, Centro de Investigación y de Estudios Avanzados del I.P.N., A.P. 14-740, C.P. 07000 México, D.F., Mexico, D.F.

Abstract

The reagents RMgCl, RLi, NaOMe and amines (R = Me or t-Bu) with bis(4-methyl-5-phenyl-1,3-oxazolidin-3-yl)methane (1) attack nucleophilically at its endo- or exocyclic methylenic groups (C-2 or C-6) giving: 3-ethyl-4-methyl-5-phenyl-1,3-oxazolidine (3), 3-neopentyl-4-methyl-5-phenyl-1,3-oxazolidine (4), 2-[neopentyl-(4-methyl-5-phenylethan-1,3-oxazolidin-3-ylmethyl)amino]-1-phenylpropan-1-ol (6), N-neopentyl norephedrine (7), 3-methoxymethyl-4-methyl-5-phenyl-1,3-oxazolidine (8), N-benzyl-(4-methyl-5-phenyl-1,3-oxazolidin-3-yl)methane (9), 2-chloropropyl-(4-methyl-5-phenyl-1,3-oxazolidin-3-ylmethyl)amine (10), 2-[(benzylamino-methyl)amino]-1-phenylpropan-1-ol (11). A high yield synthesis of 3(H)-4-methyl-5-phenyl-1,3-oxazolidine (5) is also reported.