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Volumn 13, Issue 10, 2001, Pages 731-735

Use of S-mosher acid as a chiral solvating agent for enantiomeric analysis of some trans-4-(4-fluorophenyl)-3-substituted-1-methylpiperidines by means of NMR spectroscopy

Author keywords

Chiral solvating agent; Diastereomeric salts; Enantiomeric analysis; NMR; Paroxetine; Piperidines; S Mosher acid; Spectral non equivalence

Indexed keywords

ACID; FLUORINE DERIVATIVE; MOSHER ACID; PAROXETINE; PIPERIDINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 0035149550     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10012     Document Type: Conference Paper
Times cited : (9)

References (21)
  • 1
    • 0025970140 scopus 로고
    • Paroxetine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depressive illness
    • (a) Dechant KL, Clissold SP. Paroxetine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depressive illness. Drug 1991;41:225-253.
    • (1991) Drug , vol.41 , pp. 225-253
    • Dechant, K.L.1    Clissold, S.P.2
  • 3
    • 0001262292 scopus 로고
    • (1S,3R,4S)-1-Methyl-3-(4-methoxyphenoxymethyl)-4-phenylpiperidinium chloride (FG4963): A selective inhibitor of serotonine uptake
    • Jones PG, Kennard O. (1S,3R,4S)-1-Methyl-3-(4-methoxyphenoxymethyl)-4-phenylpiperidinium chloride (FG4963): a selective inhibitor of serotonine uptake. Acta Crystallogr Sect B 1979;35:1732-1735.
    • (1979) Acta Crystallogr Sect B , vol.35 , pp. 1732-1735
    • Jones, P.G.1    Kennard, O.2
  • 4
    • 0030075033 scopus 로고    scopus 로고
    • Synthesis of 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines
    • Engelstoft M, Hansen JB. Synthesis of 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines. Acta Chem Scan 1996;50:164-169.
    • (1996) Acta Chem Scan , vol.50 , pp. 164-169
    • Engelstoft, M.1    Hansen, J.B.2
  • 6
    • 33847577885 scopus 로고
    • Process for stereospecific hydrolysis of piperidione derivatives WO 93/22284
    • (b) Curzons AD, Powell LW, Keay AM. Process for stereospecific hydrolysis of piperidione derivatives. WO 93/22284; 1993.
    • (1993)
    • Curzons, A.D.1    Powell, L.W.2    Keay, A.M.3
  • 8
    • 33847595050 scopus 로고    scopus 로고
    • Piperidine derivatives as intermediates for the preparation of paroxetine and process for their preparation. EP 0 812 827
    • Sugi K, Itaya N, Katsura T, Igi M, Yamazaki S, Ishibashi T, Yamaoka T, Kawada Y, Tagami Y. Piperidine derivatives as intermediates for the preparation of paroxetine and process for their preparation. EP 0 812 827; 1997.
    • (1997)
    • Sugi, K.1    Itaya, N.2    Katsura, T.3    Igi, M.4    Yamazaki, S.5    Ishibashi, T.6    Yamaoka, T.7    Kawada, Y.8    Tagami, Y.9
  • 9
    • 33847593491 scopus 로고    scopus 로고
    • Process for the preparation of optically enriched 4-aryl-3-hydroxymethyl substituted piperidines to be used as intermediates in the synthesis of paroxetineWO 97/24323
    • (a) Adger BM, Potter GA. Process for the preparation of optically enriched 4-aryl-3-hydroxymethyl substituted piperidines to be used as intermediates in the synthesis of paroxetine. WO 97/24323; 1996.
    • (1996)
    • Adger, B.M.1    Potter, G.A.2
  • 10
    • 33847579402 scopus 로고    scopus 로고
    • Stereoselective preparation of 3-substituted 4-aryl piperidine compounds. WO 99/07680
    • (b) Murthy KS, Rey AW. Stereoselective preparation of 3-substituted 4-aryl piperidine compounds. WO 99/07680; 1999.
    • (1999)
    • Murthy, K.S.1    Rey, A.W.2
  • 11
    • 0030009989 scopus 로고    scopus 로고
    • Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine
    • (a) Amat M, Hidalgo J, Bosch J. Synthesis of enantiopure 3,4-disubstituted piperidines. An asymmetric synthesis of (+)-paroxetine. Tetrahedron: Asymmetry 1996;7:1591-1594.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1591-1594
    • Amat, M.1    Hidalgo, J.2    Bosch, J.3
  • 13
    • 0000237404 scopus 로고
    • NMR determination of enantiomeric purity
    • Parker D. NMR determination of enantiomeric purity. Chem Rev 1991; 91:1441-1457.
    • (1991) Chem Rev , vol.91 , pp. 1441-1457
    • Parker, D.1
  • 14
    • 33845280542 scopus 로고
    • Use of carboxylic acids as chiral solvating agents for the determination of optical purity of chiral amines by NMR spectroscopy
    • Benson SC, Cai P, Colon M, Haiza MA, Tokles M, Synder JK. Use of carboxylic acids as chiral solvating agents for the determination of optical purity of chiral amines by NMR spectroscopy. J Org Chem 1988;53:5335-5341.
    • (1988) J Org Chem , vol.53 , pp. 5335-5341
    • Benson, S.C.1    Cai, P.2    Colon, M.3    Ma, H.4    Tokles, M.5    Synder, J.K.6
  • 15
    • 0006466515 scopus 로고
    • On the nature of magnetic nonequivalence of diastereomeric salts
    • Mikolajczyk M, Ejchart A, Jurczak J. On the nature of magnetic nonequivalence of diastereomeric salts. Bull Acad Pol Sci 1971;19:721-724.
    • (1971) Bull Acad Pol Sci , vol.19 , pp. 721-724
    • Mikolajczyk, M.1    Ejchart, A.2    Jurczak, J.3
  • 16
    • 0010640653 scopus 로고
    • α-methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
    • Dale JA, Dull DL, Mosher HS. α-methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 1969;34:2543-2548.
    • (1969) J Org Chem , vol.34 , pp. 2543-2548
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 18
    • 33847086300 scopus 로고
    • 15N NMR spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline
    • 15N NMR spectroscopy. 8-Benzyl-5,6,7,8-tetrahydroquinoline. J Am Chem Soc 1980;102:1166-1167.
    • (1980) J Am Chem Soc , vol.102 , pp. 1166-1167
    • Roberts, J.D.1    Dyllick-Brenzinger, R.2
  • 19
    • 37049087887 scopus 로고
    • 1,2-Diphenylethane-1,2-diamine: An effective NMR chiral solvating agent for chiral carboxylic acids
    • Fullwood R, Parker D. 1,2-Diphenylethane-1,2-diamine: an effective NMR chiral solvating agent for chiral carboxylic acids. J Chem Soc Perkin Trans 1994;2:57-64.
    • (1994) J Chem Soc Perkin Trans , vol.2 , pp. 57-64
    • Fullwood, R.1    Parker, D.2
  • 21
    • 33845281407 scopus 로고
    • Chiral molecular recognition in small bimolecular systems: A spectroscopic investigation into the nature of diastereomeric complexes
    • Pirkle WH, Pochapsky TC. Chiral molecular recognition in small bimolecular systems: a spectroscopic investigation into the nature of diastereomeric complexes. J Am Ceram Soc 1987;109:5975-5982.
    • (1987) J Am Ceram Soc , vol.109 , pp. 5975-5982
    • Pirkle, W.H.1    Pochapsky, T.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.