Birch reduction of (-)-ephedrine. Formation of a new, versatile intermediate for organic synthesis

Journal of Organic Chemistry

Volumn 69, Issue 16, 2004, Pages 5490-5493

  Zvilichovsky, Gury ^a   Gbara Haj Yahia, Isra ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AMMONIA; ESTERS; LITHIUM; SYNTHESIS (CHEMICAL);

AROMATIC RINGS; LIQUID AMMONIA;

AROMATIC COMPOUNDS;

ALDEHYDE DERIVATIVE; AMMONIA; BETA KETO ALDEHYDE; BETA KETO SIGMA METHYLAMINO ESTER; CYCLOHEXANE DERIVATIVE; EPHEDRINE; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; LITHIUM; N BENZOYL 1 (1,4 CYCLOHEXADIEN 1 YL) N METHYL 2 PROPANAMINE; S 1 (1,4 CYCLOHEXADIEN 1 YL) N METHYL 2 PROPANAMINE; UNCLASSIFIED DRUG;

ARTICLE; BIRCH REDUCTION; CHEMICAL BOND; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ORGANIC CHEMISTRY; OZONOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROTATION; STRUCTURE ANALYSIS; SYNTHESIS;

CATALYSIS; EPHEDRINE; ESTERS; LITHIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OZONE; PROPYLAMINES; STEREOISOMERISM;

EID: 3543023290     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049726u     Document Type: Article

References (15)

1. Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1 1995, 2509.
2. Zvilichovsky, G.; Gurvich, V. Tetrahedron 1995, 51, 5479.
3. Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1 1997, 1069.
4. . Zvilichovsky, G.; Gurvich, V. Tetrahedron 1997, 53, 4457.
5. Zvilichovsky, G.; Gurvich, V. Recent Res. Dev. Org. Chem. 1999, 3, 87.
6. Gbara-Haj-Yahia, I.; Zvilichovsky, G.; Seri, N. J. Org. Chem. 2004, 69, 4135.
7. c is the coalescence temperature and Δv is the separation in Hz between the signals of the two conformers. See: Paek, K.; Ihm, H.; Yun, S.; Lee, H. C.; No, K. T. J. Org. Chem. 2001, 66, 5736.
8. (a) Zvilichovsky, G.; Gurvich. V.; Segev, S. J. Org. Chem. 1995, 60, 5250.
9. (b) Zvilichovsky, G.; Gbara-Hag-Yahia, I. J. Org. Chem. 2004, 69, 4966-4973.
10. Vloon, W. J.; Kruk, C.; Pandit, U. K.; Hofs, H. P.; McVie, J. G. J. Med. Chem. 1987, 30, 20.
11. Umezawa, Y.; Morishima, H.; Saito, S.; Takita, T.; Umezawa, H.; Kobayashi, S.; Otsuka, M.; Narita, M.; Ohno, M. J. Am. Chem. Soc. 1980, 102, 6631.
12. Stubbe, J. Kozarich, J. W. Chem. Rev. 1987, 87, 1107.
13. Bauer, L.; Nambury, C. N. V. J. Org. Chem. 1961, 26, 4917.
14. Breuniger, H.; Moede, R. Pharm. Zentralh. 1969, 108, 615.
15. Zvilichovsky, G.; David, M. J. Org. Chem. 1982, 47, 295.