- Crystal of fumarate of salmeterol intermediate and preparation process thereof
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The invention discloses a crystal of fumarate of a salmeterol intermediate and a preparation process thereof. The preparation process comprises the following steps: dissolving 6-benzylamino-1-(4'-phenylbutoxy)hexane in alcohol; adding fumaric acid; carrying out heating to 50 to 60 DEG C and carrying out stirring to allow the above substance to be thoroughly dissolved; carrying out cooling to 37 to 40 DEG C within 2 to 4 h so as to allow a crystal to be precipitated, and maintaining the temperature for 2 to 3 h; then allowing the temperature to drop to 12 to 15 DEG C within 6 to 8 h; and successively carrying out ageing for 8 to 12 h, filtering and drying so as to obtain a white solid so as to obtain the fumarate of the salmeterol intermediate 6-benzylamino-1-(4'-phenylbutoxy)hexane. The crystal obtained in the invention has good stability and can be stored for a long time; the preparation process is convenient to operate and easy for industrialization; the alcohol used in the invention is a low-toxicity solvent selected from an organic solvent; and the crystal form of the fumarate of the salmeterol intermediate can be stably obtained.
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- A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation
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(R)-Salmeterol was synthesized in eight steps with salicaldehyde as the starting material. The key chiral intermediate, alcohol 5, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEG-BsDPEN or (S,S)-TsDPEN ligand and sodium formate as the hydrogen donor under mild conditions.
- Liu, Juntao,Zhou, Di,Jia, Xian,Huang, Ling,Li, Xingshu,Chan, Albert S.C.
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p. 1824 - 1828
(2008/12/22)
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- NOVEL PROCESS
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The present invention relates to processes for the preparation of 4- hydroxy-α'' -[[[6-(4-phenylbutoxy)hexyl]amino]methyl]- 1,3-benzenedimethanol 1-hydroxy-2-naphthoate (salmeterol xinafoate) (Formula (12a)), the preparation of 4-hydroxy-α''-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol (salmeterol) (Formula (11)), the preparation of protected N-[6-(4-phenylbutoxy)hexyl]amine intermediates (Formula (7)), and the preparation of 6-substituted (4-phenylbutoxy)hexane intermediates (Formula (5)), shown below, wherein X is a leaving group and Pg is a protecting group.
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Page/Page column 24-25
(2010/11/27)
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- Improved synthesis of 13C,2H3- and 2H3-salmeterol by Cs2CO3-mediated monoalkylation of a primary amine
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An abbreviated synthesis of isotopically labelled salmeterol has been achieved. The key improvement utilizes a highly selective Cs2CO3-mediated one-pot alkylation of benzylamine by 6-bromo-1-(4′-phenylbutoxy)hexane to prepare the limiting reagent, 6-N-benzylamino-1-(4′-phenylbutoxy)hexane without overalkylation. The method was applied to synthesis of the title compounds in >97 at% isotopic purity. Copyright
- Molinski, Tadeusz F.,Stanley, Scott D.
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p. 755 - 762
(2007/10/03)
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- A new synthetic approach to salmeterol
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In the present work a short and convenient route for the synthesis of salmeterol from salicylaldehyde has been developed.
- Rong, Yajing,Ruoho, Arnold E.
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p. 2155 - 2162
(2007/10/03)
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- Enantioselective synthesis of salmeterol via asymmetric borane reduction
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Enantioselective syntheses of both enantiomers of salmeterol are accomplished using asymmetric borane reductions with chiral oxazaborolidines as catalysts.
- Hett, Robert,Stare, Ragnar,Helquist, Paul
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p. 9375 - 9378
(2007/10/02)
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