A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1,2,3-oxathiazolidme-2-oxide: Practical asymmetric synthesis of (R)-sibutramine
A novel and direct approach for the asymmetric synthesis of (R)-sibutramine via chiral amine 5 using N-tosyl-1,2,3-oxathiazolidine-2-oxide (13) as a recyclable chiral auxiliary is described. Chiral sulfinate imine 16e was obtained by treatment of 13e with
Han, Zhengxu,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
p. 327 - 333
(2012/12/22)
ENANTIOSELECTIVE SYNTHESIS OF A STERICALLY HINDERED AMINE
Compounds of the formula (I) wherein R is phenyl, or phenyl substituted by Cl, Br, C1-C4alkyl or CF3; R1 is H or methyl or ethyl; R2 is H or methyl or acyl; R3 is H or methyl; R'4/sub
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Page/Page column 15-16
(2008/06/13)
A study and identification of potential by-products of sibutramine
In the synthesis and process development of sibutramine (9), the isolation and characterization of two potential by-products namely heptane dinitriles (4a-b) and bis-cyclobutyl alkylamine (10) have been studied. The key steps in the synthesis of sibutramine which have contributed to the formation of above by-products are cycloalkylation of 4-chlorophenyl acetonitrile (1) and tandem Grignard reduction on 1-(4-chlorophenyl)cyclobutyl carbonitrile (3).
Reddy, G. Om,Sarma,Chandrasekhar,Babu, J. Moses,Prasad,Raju, C.M. Haricharan
p. 488 - 492
(2013/09/08)
Synthesis of sibutramine, a novel cyclobutylalkylamine useful in the treatment of obesity, and its major human metabolites
Synthetic routes to N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-N,N-dimethylamine (sibutramine) 1 and its demethylated and hydroxylated human metabolites N-{1-[1-(4-chlorophenyl)cyclobutyl]-3-methyibutyl}-N-methylamine2, 1-[1-(4-chiorophenyl)cyclobutyl]-3-methylbutylamine 3, 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-1-ol 4 and c-3-(1-amino-3-methylbutyl)-3-(4-chlorophenyl)cyclobutan-r-1-ol 5a are described. Key steps are tandem Grignard-reduction reactions on 1-(4-chlorophenyl)cyclobutanecarbonitrile 7 and its 3-(tetrahydropyran-2-yloxy)-substituted analogue 14 and a convenient one-pot conversion of 4-chlorophenylacetonitrile 6 into the 3-hydroxycyclobutanecarbonitrile 13.
Jeffery, James E.,Kerrigan, Frank,Miller, Thomas K.,Smith, Graham J.,Tometzki, Gerald B.
p. 2583 - 2589
(2007/10/03)
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