Twisted amide reduction under Wolff-Kishner conditions: Synthesis of a benzo-1-aza-adamantane derivative

Journal of the American Chemical Society

Volumn 125, Issue 11, 2003, Pages 3268-3272

  Bashore, Crystal G ^a   Samardjiev, Ivan J ^a   Bordner, Jon ^a   Coe, Jotham W ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

WOLFF-KISHNER CONDITIONS;

DERIVATIVES; HYDROLYSIS; REDUCTION; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALCOHOL; AMIDE; AMINO ACID; BENZO 1 AZAADAMANTANE; ETHYLENE GLYCOL; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; NICOTINIC AGENT; POTASSIUM HYDROXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; MOLECULAR STABILITY; STRUCTURE ANALYSIS;

ADAMANTANE; AMIDES; AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 0037454322     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028152c     Document Type: Article

References (46)

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28. For examples of bromo-amination, see: (a) Stevens C.; Verbeke, A.; De Kimpe, N. Synlett 1998, 180-183. (b) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547-5550. (c) Horning, D. E.; Muchowski, J. M. Can. J. Chem. 1974, 52, 1321-1330 and references therein. For involvement by amides, see: (d) Sakurai, O.; Takahashi, M.; Ogiku, T.; Hayashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 35, 6317-6320. (e) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600-5602. (f) Balko, T. W.; Brinkmeyer, R. S.; Terando, N. H. Tetrahedron Lett. 1989, 30, 2045-2048. (g) Knapp, S.; Levorse, A. T.; Potenza, J. A. J. Org. Chem. 1988, 53, 4773-4779 and references therein.
29. For examples of bromo-amination, see: (a) Stevens C.; Verbeke, A.; De Kimpe, N. Synlett 1998, 180-183. (b) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547-5550. (c) Horning, D. E.; Muchowski, J. M. Can. J. Chem. 1974, 52, 1321-1330 and references therein. For involvement by amides, see: (d) Sakurai, O.; Takahashi, M.; Ogiku, T.; Hayashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 35, 6317-6320. (e) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600-5602. (f) Balko, T. W.; Brinkmeyer, R. S.; Terando, N. H. Tetrahedron Lett. 1989, 30, 2045-2048. (g) Knapp, S.; Levorse, A. T.; Potenza, J. A. J. Org. Chem. 1988, 53, 4773-4779 and references therein.
30. For examples of bromo-amination, see: (a) Stevens C.; Verbeke, A.; De Kimpe, N. Synlett 1998, 180-183. (b) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547-5550. (c) Horning, D. E.; Muchowski, J. M. Can. J. Chem. 1974, 52, 1321-1330 and references therein. For involvement by amides, see: (d) Sakurai, O.; Takahashi, M.; Ogiku, T.; Hayashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 35, 6317-6320. (e) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600-5602. (f) Balko, T. W.; Brinkmeyer, R. S.; Terando, N. H. Tetrahedron Lett. 1989, 30, 2045-2048. (g) Knapp, S.; Levorse, A. T.; Potenza, J. A. J. Org. Chem. 1988, 53, 4773-4779 and references therein.
31. For examples of bromo-amination, see: (a) Stevens C.; Verbeke, A.; De Kimpe, N. Synlett 1998, 180-183. (b) Corey, E. J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5547-5550. (c) Horning, D. E.; Muchowski, J. M. Can. J. Chem. 1974, 52, 1321-1330 and references therein. For involvement by amides, see: (d) Sakurai, O.; Takahashi, M.; Ogiku, T.; Hayashi, M.; Horikawa, H.; Iwasaki, T. Tetrahedron Lett. 1994, 35, 6317-6320. (e) Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600-5602. (f) Balko, T. W.; Brinkmeyer, R. S.; Terando, N. H. Tetrahedron Lett. 1989, 30, 2045-2048. (g) Knapp, S.; Levorse, A. T.; Potenza, J. A. J. Org. Chem. 1988, 53, 4773-4779 and references therein.
32. C-N bond lengths in 11 confirm the additional strain inherent in the bicyclic C-N (benzylic) bond: 1.627 versus 1.515, 1.532 (benzylic), and 1.512 Å; see Supporting Information and compare to an analogous quaternary ammonium salt, 2 in: Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415, Supporting Information. Efforts to equilibrate 10 and 11 via solvolysis with bromide and iodide salts failed to alter the product ratios.
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