Stereospecific displacement of 1-(pyridinyl)ethanols with amines and thiols via methanesulfonate esters; asymmetric synthesis of 1- (pyridinyl)ethylamines and sulfides

Synlett

Volumn , Issue 1, 1999, Pages 41-44

  Uenishi, Jun'ichi ^a   Takagi, Tomoko ^a   Ueno, Tetsuya ^a   Hiraoka, Takao ^a   Yonemitsu, Osamu ^a   Tsukube, Hiroshi ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

Anti AIDS drug; Chiral (pyridinyl)ethylamine; Chiral (pyridinyl)ethylsulfide; Chiral ligand; Stereospecific substitution

Indexed keywords

1 (2 PYRIDINYL) ETHANOL METHANESULFONIC ACID; 1 (2 PYRIDINYL) ETHYLAMINE; 1 (2 PYRIDINYL) SULFIDE; 6 CHLORO 2 [(1 FURO[2,3 C]PYRIDIN 5 YLETHYL)THIO] 4 PYRIMIDINAMINE; ALCOHOL DERIVATIVE; ALIPHATIC AMINE; AMINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; AROMATIC AMINE; DIMETHYL SULFOXIDE; SULFIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0032909975     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2564     Document Type: Article

References (42)

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25. Mesylate 1 was prepared from optically pure (S)-1-(2-pyridinyl)ethanols with methanesulfonyl chloride by the standard method and the chiral ethanol were obtained by lipase-catalyzed enantioselective acetylation; see Uenishi, J.; Hiraoka, T.; Hata, S.; Nishiwaki, K.; Yonemitsu, O.; Nakamura, K.; Tsukube, H. J. Org. Chem. 1998, 63, 2481.
26. 3CN ∼EtOH>benzene≫THF(slow).
27. 4, and evaporated. The residual oil was purified by column chromatography on silica gel eluted with a mixture of EtOAc and hexane.
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33. This substitution reaction in DMF was reported by Chelucci et al. (see reference 6a), but the specificity was only 66% e.e. Re-investigation of the reaction gave the product with excellent e.e. (>95%) when the mesylate was used after purification by silica gel chromatography.
34. The ORTEP view of the sulfoxide. (Formula presented)
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36. The substrates (e.e. > 95%) were prepared as an optically pure form by the same method described in our previous paper (see reference 8).
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38. Since methanesulfonate ester of α-phenethylalcohol is unstable, the substitution reaction has never been reported. See, Crossland, R. K. Servis, K. L. J. Org. Chem. 1970, 35, 3195.
39. N1 processes.
40. The optical purity of 9 was determined to be >97% by Mosher analysis.
41. Studies of asymmetric reactions using these two chiral ligands are underway in our laboratory.
42. The physical and spectroscopic data of 16 were coincident with the data reported by Morris et al. Enantiomeric purity was independently determined by HPLC using chiral column (SUMICHIRAL OA-25001).