3-Aminopyrrolidines from α-aminoacids: Total synthesis of (+)-nemonapride from D-alanine

Journal of Organic Chemistry

Volumn 73, Issue 3, 2008, Pages 1162-1164

  Cam, Thuy Hoang ^a   Viet, Hoang Nguyen ^a   Alezra, Valérie ^a   Kouklovsky, Cyrille ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DERIVATIVES; REDUCTION; SYNTHESIS (CHEMICAL);

AMINOPYRROLIDINES; BENZOIC ACID; BIRCH REDUCTION; D-ALANINE;

AMINES;

ALPHA AMINO ACID; DEXTRO ALANINE; EMONAPRIDE; PYRROLIDINE DERIVATIVE;

ARTICLE; BIRCH REDUCTION; DRUG SYNTHESIS; HYDROLYSIS; OXIDATION; REACTION ANALYSIS;

ALANINE; AMINATION; BENZAMIDES; MOLECULAR STRUCTURE; PYRROLIZIDINE ALKALOIDS;

EID: 38849172578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702278k     Document Type: Article

References (12)

1. (a) Murakami, K.; Takahashi, M.; Hirata, Y.; Takashima, M.; Iwanami, S.; Hasegawa, O.; Nozaki, Y.; Tashikawa, S.; Takeda, M.; Usuda, S. U.S. Patent 4097487, 1978.
2. (b) Takashima, M.; Iwanami, S.; Usuda, S. U.S. Patent 4210660, 1980.
3. (c) Iwanami, S.; Takashima, H.; Hirata, Y.; Hasagewa, O.; Usuda, S. J. Med. Chem. 1981, 24, 1224.
4. (a) Furuya, T.; Iwanami, S.; Takenaka, A.; Sasada, Y. Bull. Chem. Soc. Jpn 1982, 55, 2321.
5. (b) Yamamoto, M.; Usuda, S.; Tachikawa, S.; Maeno, H. Neurophamacology 1982, 21, 945.
6. Huang, P. Q.; Wang, S. L.; Zheng, H.; Fei, X. S. Tetrahedron Lett. 1997, 38, 271.
7. Shibugushi, T.; Mihara, H.; Kuramochi, A.; Ohshima, T.; Shibasaki, M. Chem. Asian J. 2007, 2, 794.
8. Hoang, C. T.; Alezra, V.; Guillot, R.; Kouklovsky, C. Org. Lett. 2007, 9, 2521.
9. For the synthesis and properties of 3-aminopyrrolidines, see: (a) Davies, S. G.; Garner, A. C.; Goddard, E. C.; Kruchinin, D.; Roberts, P. M.; Rodriguez-Solla, H.; Smith, A. D. Chem. Commun. 2006, 2664 and references cited therein,
10. (b) See also: Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 7, 5861.
11. The enantiomeric purity of 8 was checked by HPLC analysis on a chiral column and comparison with a racemic standard (prepared according to the same synthetic sequence from racemic alanine) and was found to be >99%.
12. Since there is a slight difference in the optical rotation of synthetic nemonapride 1 and literature data, the enantiomeric purity of 1 was checked by HPLC analysis on a chiral column with comparison to a racemic standard (prepared according to the same synthetic sequence from racemic alanine) and was found to be >99%.