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【结 构 式】

【分子编号】11971

【品名】(1R)-3-[Benzyl(methyl)amino]-1-phenyl-1-propanol

【CA登记号】

【 分 子 式 】C17H21NO

【 分 子 量 】255.35988

【元素组成】C 79.96% H 8.29% N 5.49% O 6.27%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The synthesis of (R)-fluoxetine hydrochloride has been described: The condensation of acetophenone (I) with N-benzyl-N-methylamine (II) and formaldehyde by means of concentrated HCl in refluxing methanol gives 3-(N-benzyl-N-methylamino)propiophenone (III), which is asymmetrically reduced with H2 at 30 Atm. over [Rh(1,5-cyclooctadiene)Cl] and the chiral phosphine (2S,4S)-1-(N-methylcarbamoyl)-4-(dicyclohexylphosphino)-2-(diphenylphos phinomethyl)pyrrolidine in methanol yielding (R)-3-(N-benzyl-N-methylamino)-1-phenyl-1-propanol (IV). The debenzylation of (IV) with H2 over Pd/C in ethanol affords (R)-3-(methylamino)-1-phenyl-1-propanol (V), which is finally condensed with 1-chloro-4-(trifluoromethyl)benzene (VI) by means of NaH in dimethylacetamide.

1 Sakuraba, S.; Achiwa, K.; Efficient asymmetric hydrogenation of beta- and gamma-amino ketone derivatives leading to practical synthesis of fluoxetine and eprozinol. Chem Pharm Bull 1995, 43, 5, 748.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10317 Acetophenone 98-86-2 C8H8O 详情 详情
(II) 11969 N-Methyl(phenyl)methanamine; N-Benzyl-N-methylamine; N-Methylbenzylamine 103-67-3 C8H11N 详情 详情
(III) 11970 3-[Benzyl(methyl)amino]-1-phenyl-1-propanone; 3-(N-Benzyl-N-methylamino)propiophenone 5409-62-1 C17H19NO 详情 详情
(IV) 11971 (1R)-3-[Benzyl(methyl)amino]-1-phenyl-1-propanol C17H21NO 详情 详情
(V) 11972 (1R)-3-(Methylamino)-1-phenyl-1-propanol; (R)-3-Hydroxy-N-methyl-3-phenyl propylamine 42142-52-9 C10H15NO 详情 详情
(VI) 11973 1-Chloro-4-(trifluoromethyl)benzene; 4-Chlorobenzotrifluoride 98-56-6 C7H4ClF3 详情 详情
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