A simple and efficient procedure for the synthesis of optically active 4-methoxy-α-methylphenylethylamine from tyrosine

Synthetic Communications

Volumn 28, Issue 11, 1998, Pages 1935-1945

  Kohno, Harumichi ^a   Iwakuma, Takeo ^a,b   Yamada, Koichiro ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^b ZERIA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARMOTEROL; PHENETHYLAMINE DERIVATIVE; TYROSINE;

ARTICLE; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031864596     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808007167     Document Type: Article

References (10)

1. We will soon submit the manuscript related to synthetic studies of TA-2005.
2. Murase, K. Mase, T. Ida, H. Takahasi, K. and Murakami, M. Chem. Pharm.Bull. 1978, 26, 1123.
3. Nichols, D.E. Barfknecht, C.F. and Rusterholz, D.B. J. Med. Chem. 1973, 16, 480 .
4. After finishing our research, Donner B.G. reported a similar conversion of chiral aminoacid to optically active α-methylamines by Raney nickel reduction of N-Boc protected amino acid-derived thioethers. See ref. Donner, B.G. Tetrahedron Lett. 1995, 36, 1223.
5. Seki, K. Koga, K. and Yamada, S. Chem. Pharm. Bull., 1967, 15, 1948.
6. The tosylation of (S)-3 by using an usual method (TsCl (1.2eq) / pyridne, 0°C, 1.5hr) gave the desired (S)-4 in lower yield (61.8 %) compared to this PTC method.
7. Fujimoto, Y. and Tatsuno, T. Tetrahedron Lett., 1976, 3325.
8. Kocovsky, P. and Cerny, V. Coll. Czechoslov. Chem. Commun. 1979, 44, 234.
9. 2 antagonists was reported by Kohno H. et al.; See Abstracts Papers of 15th Symposium on Med.Chem. (Osaka, Japan), 1994, pp. 151-152 .
10. Wada, H. Ishii, K. Tsumagai, N. Matsuo, M. and Matsumoto, M. Japan Kokai, 59-76051 (1984).