A Diastereospecific Synthesis of 2-Methyl-5β-phenyl-5α-carbethoxy-2-azabicyclo[2.2.1]heptane: A Ring-Constrained Analogue of Meperidine

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 418-419

  Husbands, Stephen M ^a   Kline, Richard H ^a   Allen, Andrew C ^a,b   Newman, Amy Hauck ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYL 5BETA PHENYL 5ALPHA CARBETHOXY 2 AZABICYCLO[2.2.1]HEPTANE; MU OPIATE RECEPTOR AGONIST; PETHIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032489042     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971791z     Document Type: Article

References (9)

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2. Izenwasser, S.; Newman, A. H.; Cox, B. M.; Katz, J. L. Eur. J. Pharmacol. 1996, 297, 9.
3. Katz, J. L.; Newman, A. H.; Izenwasser, S. Pharmacol. Biochem. Behav. 1997, 57, 1.
4. Madras, B. K.; Fahey, M. A.; Bergman, J.; Canfield, D. R.; Spealman, R. D. J. Pharmacol. Exp. Ther. 1989, 251, 131.
5. Portoghese, P. S.; Mikhail, A. A.; Kupferberg, H. J. J. Med. Chem. 1968, 11, 219.
6. Daum, S. J.; Martini, C. M.; Kullnig, R. K.; Clarke, R. L. J. Med. Chem. 1975, 18, 196.
7. Remuzon, P. Tetrahedron 1996, 52, 13803.
8. The configuration at C-5 was determined by NOE experiments. Irradiation of the H-6 exo, but not the H-6 endo, proton caused an enhancement of the signal for the phenyl ring.
9. See the Supporting Information. Newman, A. H.; Kline, R. H.; Allen, A. C.; Izenwasser, S.; George, C.; Katz, J. L. J. Med. Chem. 1995, 38, 3933.