Synthesis of tertiary amines using a polystyrene (REM) resin

Journal of the American Chemical Society

Volumn 119, Issue 14, 1997, Pages 3288-3295

  Brown, Angus R ^a   Rees, David C ^a   Rankovic, Zoran ^a   Morphy, J Richard ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030921936     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963829f     Document Type: Article

References (23)

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2. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385.
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11. This estimate was obtained by searching the World Drugs Index (Derwent Information Ltd.) for compounds with a tradename which also contain a tertiary amine group.
12. The parallel synthesis of tertiary amines has been reported previously using (a) an ester or amide tether to polystyrene resin (Green, J. J. Org. Chem. 1995, 60, 4287) or (b) solution phase methods incorporating solid phase scavengers (Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193).
13. The parallel synthesis of tertiary amines has been reported previously using (a) an ester or amide tether to polystyrene resin (Green, J. J. Org. Chem. 1995, 60, 4287) or (b) solution phase methods incorporating solid phase scavengers (Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tetrahedron Lett. 1996, 37, 7193).
14. β-Eliminations of carboxylic acids from a solid support have been reported previously: (a) Katti, S. B.; Misra, P. K.; Haq, W.; Mathur, K. B. J. Chem. Soc., Chem. Commun. 1992, 843. (b) Eritja, R.; Robles, J.; Fernandez-Forner, D.; Albericio, F.; Giralt, E.; Pedroso, E. Tetrahedron Lett. 1991, 32, 1511.
15. β-Eliminations of carboxylic acids from a solid support have been reported previously: (a) Katti, S. B.; Misra, P. K.; Haq, W.; Mathur, K. B. J. Chem. Soc., Chem. Commun. 1992, 843. (b) Eritja, R.; Robles, J.; Fernandez-Forner, D.; Albericio, F.; Giralt, E.; Pedroso, E. Tetrahedron Lett. 1991, 32, 1511.
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