合成路线:2-Aminoacetophenone.HCl (IV) is prepared from acetophenone (I) via 2-bromoacetophenone (II) and the quaternary urotropine salt (III).Acetylation of (IV) with acetic anhydride in water in the presence of sodium hydrogen carbonate yields 2-acetamidoacetophenone (V),which is converted to 2-acetamido-3-hydroxypropiophenone.HCl (VI) with formaldehyde in water.After removing the acetyl group with hydrochloric acid in ethanol,2-amino-3-hydroxypropiophenone.HCl (VII) is formed,which is reduced with hydrogen over Pd/C in methanol to rac-erythro-2-amino-1-phenyl-1,3-propanediol.HCl (VIII).Reductive condensation of the corresponding base (IX) with phenoxyacetone (X) and hydrogen over PtO2 affords a mixture of aminodiols epimeric at C-1' (XI).(XI) is finally converted to the corresponding hydrochloride salts,from which the salt of the less soluble [1R*,2S*(S*)]-stereoisomer,i.e.,solpecainol is isolated by crystallization.Structure and purity of solpecainol have been confirmed by x-ray crystallography and HPLC-MS.
参考文献标题:Comparison and evaluation of derivatization methods for gas chromatographic determination of various propanediols
文献作者:Vida,L.; Szepesy,L.; Lakszner,K.
参考来源:Chromatographia 1984,19304
合成路线:2-Aminoacetophenone.HCl (IV) is prepared from acetophenone (I) via 2-bromoacetophenone (II) and the quaternary urotropine salt (III).Acetylation of (IV) with acetic anhydride in water in the presence of sodium hydrogen carbonate yields 2-acetamidoacetophenone (V),which is converted to 2-acetamido-3-hydroxypropiophenone.HCl (VI) with formaldehyde in water.After removing the acetyl group with hydrochloric acid in ethanol,2-amino-3-hydroxypropiophenone.HCl (VII) is formed,which is reduced with hydrogen over Pd/C in methanol to rac-erythro-2-amino-1-phenyl-1,3-propanediol.HCl (VIII).Reductive condensation of the corresponding base (IX) with phenoxyacetone (X) and hydrogen over PtO2 affords a mixture of aminodiols epimeric at C-1' (XI).(XI) is finally converted to the corresponding hydrochloride salts,from which the salt of the less soluble [1R*,2S*(S*)]-stereoisomer,i.e.,solpecainol is isolated by crystallization.Structure and purity of solpecainol have been confirmed by x-ray crystallography and HPLC-MS.
参考文献标题:Solpecainol Hydrochloride
文献作者:Ber閚yi,E.; Pet骳z,L.; Blask? G.; N骻r醖i,M.
参考来源:Drugs Fut 1991,16(6),514
合成路线:2-Aminoacetophenone.HCl (IV) is prepared from acetophenone (I) via 2-bromoacetophenone (II) and the quaternary urotropine salt (III).Acetylation of (IV) with acetic anhydride in water in the presence of sodium hydrogen carbonate yields 2-acetamidoacetophenone (V),which is converted to 2-acetamido-3-hydroxypropiophenone.HCl (VI) with formaldehyde in water.After removing the acetyl group with hydrochloric acid in ethanol,2-amino-3-hydroxypropiophenone.HCl (VII) is formed,which is reduced with hydrogen over Pd/C in methanol to rac-erythro-2-amino-1-phenyl-1,3-propanediol.HCl (VIII).Reductive condensation of the corresponding base (IX) with phenoxyacetone (X) and hydrogen over PtO2 affords a mixture of aminodiols epimeric at C-1' (XI).(XI) is finally converted to the corresponding hydrochloride salts,from which the salt of the less soluble [1R*,2S*(S*)]-stereoisomer,i.e.,solpecainol is isolated by crystallization.Structure and purity of solpecainol have been confirmed by x-ray crystallography and HPLC-MS.
参考文献标题:
文献作者:
参考来源:Central Res.Inst.Chem.Hung.Acad.Sci.Report (27.10.1983) 1983,
产品链接: CAS No. 68567-30-6››