合成路线:In a related process,the racemic piperidinyl ketone (VII) was initially resolved employing D-tartaric acid.The target (2S)-piperidinyl propanone (VIII) was then diastereoselectively reduced to the (1S,2S)-alcohol (IX) employing LiBH4 in EtOH.Finally,debenzylation of (IX) by catalytic hydrogenolysis yielded the title compound
合成路线:In a related process,the racemic piperidinyl ketone (VIII) was initially resolved employing D-tartaric acid and then subjected to a diastereoselective reduction to the (1S,2S)-alcohol (IX) employing LiBH4 in EtOH.Finally,debenzylation of (IX) by catalytic hydrogenolysis with Pd/C in EtOH and methanesulfonic acid,followed by addition of water,yielded the title compound
参考文献标题:Process for the preparation of the mesylate salt trihydrate of 1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol and intermediates useful therefor
文献作者:Walinsky,S.W.; Rainville,J.P.; Sinay,T.G.Jr.(Pfizer Products Inc.)
参考来源:EP 1149831
合成路线:4-Hydroxypropiophenone (I) was protected as the triisopropylsilyl ether (II) and subsequently brominated with elemental bromine in CCl4 .The resultant bromo ketone (III) was subsequently coupled with 4-hydroxy-4-phenylpiperidine (IV) to afford the racemic amino ketone (V).This was stereoselectively reduced with NaBH4 in EtOH yielding the threo-amino alcohol (VI).Then,desilylation of (VI) with tetrabutylammonium fluoride furnished the racemic phenol compound.Resolution into the enantiomers has been reported by formation of the corresponding D-tartaric acid salts
合成路线:4-Hydroxypropiophenone (I) was protected as the triisopropylsilyl ether (II) and subsequently brominated with elemental bromine in CCl4.The resultant bromo ketone (III) was subsequently coupled with 4-hydroxy-4-phenylpiperidine (IV) to afford the racemic amino ketone (V).This was stereoselectively reduced with NaBH4 in EtOH yielding the threo-amino alcohol (VI).Then,desilylation of (VI) with tetrabutylammonium fluoride furnished the racemic phenol compound.Resolution into the enantiomers has been reported by formation of the corresponding D-tartaric acid salts.Finally,the title product was obtained by dissolving D-(-)-tartaric salt (VII) in water in the presence of methanesulfonic acid
参考文献标题:Process for the preparation of the mesylate salt trihydrate of 1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-1-propanol
文献作者:Walinsky,S.W.; Rainville,J.P.; Sinay,T.G.Jr.(Pfizer Products Inc.)
参考来源:EP 1151995
合成路线:4-Hydroxypropiophenone (I) was protected as the triisopropylsilyl ether (II) and subsequently brominated with elemental bromine in CCl4 .The resultant bromo ketone (III) was subsequently coupled with 4-hydroxy-4-phenylpiperidine (IV) to afford the racemic amino ketone (V).This was stereoselectively reduced with NaBH4 in EtOH yielding the threo-amino alcohol (VI).Then,desilylation of (VI) with tetrabutylammonium fluoride furnished the racemic phenol compound.Resolution into the enantiomers has been reported by formation of the corresponding D-tartaric acid salts
合成路线:4-Hydroxypropiophenone (I) was protected as the triisopropylsilyl ether (II) and subsequently brominated with elemental bromine in CCl4.The resultant bromo ketone (III) was subsequently coupled with 4-hydroxy-4-phenylpiperidine (IV) to afford the racemic amino ketone (V).This was stereoselectively reduced with NaBH4 in EtOH yielding the threo-amino alcohol (VI).Then,desilylation of (VI) with tetrabutylammonium fluoride furnished the racemic phenol compound.Resolution into the enantiomers has been reported by formation of the corresponding D-tartaric acid salts.Finally,the title product was obtained by dissolving D-(-)-tartaric salt (VII) in water in the presence of methanesulfonic acid
参考文献标题:(1S,2S)-1-(4-Hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: A potent new neuroprotectant which blocks N-methyl-D-aspartate responses
文献作者:Chenard,B.L.; Bordner,J.; Butler,T.W.; Chambers,L.K.; Collins,M.A.; De Costa,D.L.; Ducat,M.F.; Dumont,M.L.; Fox,C.B.; Mena,E.E.; et al.
参考来源:J Med Chem 1995,38(16),3138
产品链接: CAS No. 134234-12-1›› 产品链接: CAS No.134234-13-2››