N,N′-Transphthaloylation in a Monoprotected Diamine

Abstract

A convenient and simple method is described for formally transferring a phthaloyl protecting group from one amino group to another in an unsymmetrical diamine. The NMR spectra of some of the amido intermediates reveal that, at room temperature, there is restricted rotation around N-C=O and, in some cases, C-C=O bonds in these molecules.

Key words

N-phthaloyl protecting groups - transphthaloylation - NMR spectra - restricted rotation - hindered amines

References

• 1a McCormick JE. McElhinney RS. J. Chem. Res., Synop.  1981,  12 ; J. Chem. Res., Miniprint 1981, 256
• 1b McElhinney RS. McCormick JE. Lucey NM. Canc. Treat. Rev.  1988,  15:  73 
• 2 Lucey NM. McCormick JE. McElhinney RS. J. Chem. Soc., Perkin Trans. 1  1990,  795 
• 3 McCormick JE. McElhinney RS. J. Chem. Res., Synop.  1983,  176 ; J. Chem. Res., Miniprint 1983, 736
• 4a Freidinger RM. Hinkle JS. Perlow DS. Arison BH. J. Org. Chem.  1983,  48:  77 
• 4b Sakaitani M. Ohfune Y. J. Org. Chem.  1990,  55:  870 
• 5a Bergeron RJ. Acc. Chem. Res.  1986,  19:  105 
• 5b Kuksa V. Buchan R. Lin PKT. Synthesis  2000,  1189 
• 5c Theodoridis G. Tetrahedron  2000,  56:  2339 
• 6a Erbeck S. Liang X. Krieger R. Prinzbach H. Eur. J. Org. Chem.  1998,  481 
• 6b Debenham J. Rodebaugh R. Fraser-Reid B. Liebigs Ann./Recl.  1997,  791 
• 6c Nilsson M. Norberg T. Carbohydr. Res.  2000,  327:  261 
• 6d Hermann T. Angew .Chem. Int. Ed.  2000,  39:  1890 
• 7 Perron YG. Minor WF. Crast LB. Gourevitch A. Lein J. Cheney LC. J. Med. Pharm. Chem.  1962,  5:  1016 
• 8 Metha NB. Brooks RE. Strelitz JZ. Horodniak JW. J. Org. Chem.  1963,  28:  2843 
• 9 Sterk L. Hasko J. Nador K. Arzneim. Forsch.  1968,  18:  798 
• 10 Astleford B. Weigel LO. Tetrahedron Lett.  1991,  32:  3301 
• 11 Curley OMS. McCormick JE. McElhinney RS. McMurry TBH. Arkivoc  2003,  (vii):  180 
• 12a McCormick JE. McElhinney RS. Proc. R. Ir. Acad., Sect. B: Biol. Geol. Chem. Sci.  1989,  89:  213 
• 12b McCormick JE. McElhinney RS. McMurry TBH. J. Chem. Res., Synop.  1991,  138 ; J. Chem. Res., Miniprint 1991, 1216
• 13 McCormick JE. McElhinney RS. J. Chem. Res., Synop.  1981,  310 ; J. Chem. Res., Miniprint 1981, 3601