One-pot synthesis of homotryptamines from indoles

Tetrahedron Letters

Volumn 45, Issue 19, 2004, Pages 3803-3805

  Denhart, Derek J ^a   Mattson, Ronald J ^a   Ditta, Jonathan L ^a   Macor, John E ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

Homotryptamine; Indole; Organic catalysis; Serotonin

Indexed keywords

ACROLEIN; INDOLE DERIVATIVE; TRYPTAMINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REDUCTION;

EID: 1842861668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.070     Document Type: Article

References (13)

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2. Brodfuehrer P.R., Chen B., Sattleberg T.R., Smith P.R., Reddy J.P., Stark D.R., Quinlan S.L., Reid J.G., Thottathil J.K., Wang S. J. Org. Chem. 62:1997;9192.
3. Suvarov N.N., Mura Sheva V.S. Meditsinskaya Promyshlennost SSSR. 15:1961;6.
4. Basanagoudar L.D., Siddappa S. J. Karnatak Univ. 17:1972;33.
5. (c) Hofmann, A.; Troxler, F. Swiss Patent 380129, 1964;
6. (d) Hofman, A.; Troxler, F. Swiss Patent 379505, 1964.
7. Kuehne M.E., Cowen S.D., Xu F., Borman L.S. J. Org. Chem. 66:2001;5303.
8. Indole-3-propionaldehydes with an additional substituent at the 3 position of the propionaldehyde appear to be more stable than the similar molecules lacking this substitution, based on unpublished results.
9. Austin J.F., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;1172.
10. Catalyst 3 is available from commercial sources; catalyst 4 according to: Northrup A.B., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;2458.
11. 1H NMR before use. The use of freshly distilled acrolein did not produce significant improvement in yield or purity.
12. 3) δ 9.83 (t, J=1.4 Hz, 1H), 8.01 (br s, 1H), 7.91 (t, J=1.0 Hz, 1H), 7.43 (dd, J=8.4, 1.5 Hz, 1H), 7.13 (d, J=8.6 Hz, 1H), 6.95 (t, J=1.0 Hz, 1H), 3.05 (t, J=7.2 Hz, 2H), 2.82 (td, J=7.2, 1.2 Hz, 2H); MS (EI) 256.21.
13. 3) δ 8.12 (br s, 1H), 7.55 (d, J=1.9 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.11 (dd, J=8.4, 2.0 Hz, 1H), 6.99 (t, J=1.2 Hz, 1H), 2.72 (t, J=7.5 Hz, 2H), 2.35 (t, J=7.4 Hz, 2H), 2.24 (s, 6H), 1.86 (pentet, J=7.5 Hz, 2H); MS (EI) 236.99.