On the Ritter reaction of cyclic hydroxyamines: Synthesis of conformationally-restricted reduced amide dipeptide isosteres

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1297-1300

  Taylor, G Mark ^a   Baker, Stewart J ^a   Gedney, Andrea ^a   Pearson, David J ^a   Sibley, Graham E M ^a  

^a ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; PIPERIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030023743     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02378-X     Document Type: Article

References (24)

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19. The regiochemistry of the double bond was assigned by n.O.e. difference experiments.
20. For a review of the Hofmann elimination, see: Cope, A.C.; Trumbull, E.R. Org. React. 1960, 11, 317.
21. It is interesting to note that attempts to form (20) directly from the carboxylic acid (18) by alkylation of the dianion under a variety of conditions were unsuccessful.
22. Radhakrishna, A.S.; Parham, M.E.; Riggs, R.M.; Loudon, G.M. J. Org. Chem. 1979, 44, 1746.
23. The more direct approach of converting acid (20) to the amine (22) directly via the Schmidt rearrangement using DPPA (Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151) was unsuccessful.
24. All compounds gave satisfactory analytical data and the sequence shown in Scheme 1 could be performed on a multi-gramme scale.