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Volumn 42, Issue 4, 2012, Pages 589-598

General strategy for large-scale synthesis of (+)-rivastigmine and (+)-NPS R-568

Author keywords

(R) (+) 1 Phenylethylamine; (S) ( ) 1 phenylethylamine; Titanium tetra isopropoxide

Indexed keywords

BENZYLAMINE; RIVASTIGMINE; TECALCET;

EID: 80054742102     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.527425     Document Type: Article
Times cited : (12)

References (26)
  • 1
    • 25544431877 scopus 로고    scopus 로고
    • Chiral business
    • Rouhi, A. M. Chiral business. Chem. Eng. News 2003, 81(18), 45-55.
    • (2003) Chem. Eng. News , vol.81 , Issue.18 , pp. 45-55
    • Rouhi, A.M.1
  • 2
    • 0031718551 scopus 로고    scopus 로고
    • Clinical pharmacology of rivastigmine: A new-generation acetylcholinesterase inhibitor for the treatment of Alzheimer's disease
    • Polinsky, R. Clinical pharmacology of rivastigmine: A new-generation acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. Clin. Ther. 1998, 20, 634-647.
    • (1998) Clin. Ther. , vol.20 , pp. 634-647
    • Polinsky, R.1
  • 4
    • 0001427257 scopus 로고
    • Calcimimetics: Structurally and mechanically novel compounds that inhibit hormonr secretion from parathyroid cells
    • Steffey, M. E.; Fox, J.; VanWagenen, B. C.; Delmar, E. G.; Balandrin, M. F.; Nemeth, E. F. Calcimimetics: Structurally and mechanically novel compounds that inhibit hormonr secretion from parathyroid cells. J. Bone Miner. Res. 1993, 8, S175.
    • (1993) J. Bone Miner. Res. , vol.8
    • Steffey, M.E.1    Fox, J.2    VanWagenen, B.C.3    Delmar, E.G.4    Balandrin, M.F.5    Nemeth, E.F.6
  • 7
    • 67650090422 scopus 로고    scopus 로고
    • Novel convenient synthesis of rivastigmine
    • For the synthesis of rivastigmine, see: (a) Hu, M.; Zhang, F.-L.; Xie, M.-H. Novel convenient synthesis of rivastigmine. Synth. Commun. 2009, 39, 1527-1533.
    • (2009) Synth. Commun. , vol.39 , pp. 1527-1533
    • Hu, M.1    Zhang, F.-L.2    Xie, M.-H.3
  • 8
    • 80054742749 scopus 로고    scopus 로고
    • Novel process for the preparation of aminoalkyl phenyl carbamates
    • Abhay, G.; Mangesh, M.; Sanjay, P. R. Novel process for the preparation of aminoalkyl phenyl carbamates. WO2005061446, 2005.
    • (2005) WO2005061446
    • Abhay, G.1    Mangesh, M.2    Sanjay, P.R.3
  • 9
    • 0345306324 scopus 로고    scopus 로고
    • Asymmetric catalytic synthesis of a-chiral amines using a novel bis(phosphine) monoxide chiral ligand
    • Boeaio, A. A.; Pytkowicz, J.; Cote, A.; Charette, A. B. Asymmetric, catalytic synthesis of a-chiral amines using a novel bis(phosphine) monoxide chiral ligand. J. Am. Chem. Soc. 2003, 125, 14260-14261.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14260-14261
    • Boeaio, A.A.1    Pytkowicz, J.2    Cote, A.3    Charette, A.B.4
  • 10
    • 80054757765 scopus 로고    scopus 로고
    • A method of production of (-)-(S)-3-[1-(dimethylamino)ethyl]phenyl-N- methyl-carbamate
    • Hana, S.; Josef, H.; Stanislav, S. A method of production of (-)-(S)-3-[1-(dimethylamino)ethyl]phenyl-N-methyl-carbamate. WO2004037771, 2004.
    • (2004) WO2004037771
    • Hana, S.1    Josef, H.2    Stanislav, S.3
  • 11
    • 80054725117 scopus 로고    scopus 로고
    • Process for preparation of rivastigmine and tartrate
    • Ma, D. W.; Pan, Q. B.; Pan, S. Process for preparation of rivastigmine and tartrate. WO2007025481, 2007.
    • (2007) WO2007025481
    • Ma, D.W.1    Pan, Q.B.2    Pan, S.3
  • 13
    • 80054736003 scopus 로고
    • Phenylcarbamates
    • Enz, A. Phenylcarbamates. GB2203040, 1988.
    • (1988) GB2203040
    • Enz, A.1
  • 14
    • 80054739708 scopus 로고    scopus 로고
    • Method of obtaining phenylcarbamates
    • Method of obtaining phenylcarbamates. EP1939172, 2008.
    • (2008) EP1939172
  • 15
    • 68049104239 scopus 로고    scopus 로고
    • Chemoenzymatyic synthesis of rivastigmine based on lipase-catalyzed process
    • Juan, M.-S.; Marja, R.-M.; Eduardo, B.; Vicente, G.-F.; Vicente, G. Chemoenzymatyic synthesis of rivastigmine based on lipase-catalyzed process. J. Org. Chem. 2009, 74, 5304-5310.
    • (2009) J. Org. Chem. , vol.74 , pp. 5304-5310
    • Juan, M.-S.1    Marja, R.-M.2    Eduardo, B.3    Vicente, G.-F.4    Vicente, G.5
  • 16
    • 77951873910 scopus 로고    scopus 로고
    • Chemoenzymatyic synthesis of rivastigmine via dynamic resolution as a key step
    • Han, K.; Kim, C.; Park, J. Kim, M.-J. Chemoenzymatyic synthesis of rivastigmine via dynamic resolution as a key step. J. Org. Chem. 2010, 75, 3105-3108.
    • (2010) J. Org. Chem. , vol.75 , pp. 3105-3108
    • Han, K.1    Kim, C.2    Park J. Kim, M.-J.3
  • 17
    • 77954244523 scopus 로고    scopus 로고
    • Chemoenzymatyic synthesis of calcimimetic (+)-NPS R-568 via asymmetric reductive acylation of ketoxime intermediate
    • Han, K.; Kim, Y.; Park, J.; Kim, M.-J. Chemoenzymatyic synthesis of calcimimetic (+)-NPS R-568 via asymmetric reductive acylation of ketoxime intermediate. Tetrahedron Lett. 2010, 51, 3536-3537.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 3536-3537
    • Han, K.1    Kim, Y.2    Park, J.3    Kim, M.-J.4
  • 18
    • 40949111365 scopus 로고    scopus 로고
    • Ferńndez, I.; Valdivia, V.; Khiar, N. N-Isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines expeditive asymmetric synthesis of calcimimetic (+)-NPS R-568
    • Ferńndez, I.; Valdivia, V.; Khiar, N. N-Isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines expeditive asymmetric synthesis of calcimimetic (+)-NPS R-568. J. Org. Chem. 2008, 73, 745-748.
    • (2008) J. Org. Chem. , vol.73 , pp. 745-748
  • 19
    • 4043070494 scopus 로고    scopus 로고
    • Enantioselective synthesis of primary 1-(aryl)alkyl amines by nucleophilic 1,2 addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein coupled receptor ligands
    • Atobe, M.; Yamazaki, N.; Kibayashi, C. Enantioselective synthesis of primary 1-(aryl)alkyl amines by nucleophilic 1,2 addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein coupled receptor ligands. J. Org. Chem. 2004, 69, 5595-5607.
    • (2004) J. Org. Chem. , vol.69 , pp. 5595-5607
    • Atobe, M.1    Yamazaki, N.2    Kibayashi, C.3
  • 20
    • 0035939471 scopus 로고    scopus 로고
    • Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)alkylamines and application to a synthesis of calcimimetic(+)-NPS R-568 and its thio analogue
    • Yamazaki, N.; Atobe, M.; Kibayashi, C. Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)alkylamines and application to a synthesis of calcimimetic(+)-NPS R-568 and its thio analogue. Tetrahedron Lett. 2001, 42, 5029-5032.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5029-5032
    • Yamazaki, N.1    Atobe, M.2    Kibayashi, C.3
  • 21
    • 0033548461 scopus 로고    scopus 로고
    • Synthesis of NPS R-568 utilizing titanium-catalyzed asymmetric hydrosilylation
    • Hansen, M. C.; Buchwald, S. L. Synthesis of NPS R-568 utilizing titanium-catalyzed asymmetric hydrosilylation. Tetrahedron Lett. 1999, 40, 2033-2034.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2033-2034
    • Hansen, M.C.1    Buchwald, S.L.2
  • 22
    • 0032555026 scopus 로고    scopus 로고
    • The addition of amines to diisobutylaluminum-imine complexes: Preparation of NPS R- 568 hydrochloride
    • Barmore, R. M.; Logan, S. R.; VanWagenen, B. C. The addition of amines to diisobutylaluminum-imine complexes: Preparation of NPS R- 568 hydrochloride. Tetrahedron Lett. 1998, 39, 3451-3454.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3451-3454
    • Barmore, R.M.1    Logan, S.R.2    VanWagenen, B.C.3
  • 23
    • 80054731006 scopus 로고    scopus 로고
    • Method for producing o tically active aminoalkyl phenols
    • Klaus, D. Method for producing o tically active aminoalkyl phenols. WO2006136538, 2006.
    • (2006) WO2006136538
    • Klaus, D.1
  • 24
    • 40949111365 scopus 로고    scopus 로고
    • N-Isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines: Expeditive asymmetric synthesis of calcimimetic (+)-NPS R- 568
    • Fernandez, I.; Valdivia, V.; Khiar, N. N-Isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines: Expeditive asymmetric synthesis of calcimimetic (+)-NPS R- 568. J. Org. Chem. 2008, 73, 745-748.
    • (2008) J. Org. Chem. , vol.73 , pp. 745-748
    • Fernandez, I.1    Valdivia, V.2    Khiar, N.3
  • 25
    • 0141630303 scopus 로고    scopus 로고
    • Highly regioselective hydrogenolysis of bis(a -methylbenzyl)amine derivatives affected by the trifluoromethyl substituent on the aromatic ring
    • Kanai, M.; Yasumoto, M.; Kuriyama, Y.; Inomiya, K.; Katsuhara, Y.; Higashiyama, K.; Ishii, A. Highly regioselective hydrogenolysis of bis(a -methylbenzyl)amine derivatives affected by the trifluoromethyl substituent on the aromatic ring. Org. Lett. 2003, 5, 1007-1010.
    • (2003) Org. Lett. , vol.5 , pp. 1007-1010
    • Kanai, M.1    Yasumoto, M.2    Kuriyama, Y.3    Inomiya, K.4    Katsuhara, Y.5    Higashiyama, K.6    Ishii, A.7
  • 26
    • 33748733399 scopus 로고    scopus 로고
    • Asymmetric 1,3-dipolar cycloaddition of optically active trifluoromethylated a,b-unsaturated aryl sulfones with nitrones: The use of o-dialkylaminoethyl chiralauxiliaries
    • Tsuge, H.; Okano, T.; Eguchi, S.; Kimoto, H. Asymmetric 1,3-dipolar cycloaddition of optically active trifluoromethylated a,b-unsaturated aryl sulfones with nitrones: The use of o-dialkylaminoethyl chiralauxiliaries. J. Chem. Soc., Perkin Trans. 1 1997, 10, 1581- 1586.
    • (1997) J. Chem. Soc. Perkin Trans. 1 , vol.10 , pp. 1581-1586
    • Tsuge, H.1    Okano, T.2    Eguchi, S.3    Kimoto, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.