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【结 构 式】

【分子编号】30993

【品名】3-(4-fluorophenyl)pyrrolidine

【CA登记号】

【 分 子 式 】C10H12FN

【 分 子 量 】165.2104232

【元素组成】C 72.7% H 7.32% F 11.5% N 8.48%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The sulfonylation of 1-benzylpyrrolidin-3-ol by means of mesyl or tosyl chlorides gives the corresponding sulfonates (II) or (III), which are condensed with the bis(4-fluorophenyl)cuprate lithium (IV) yielding 1-benzyl-3-(4-fluorophenyl) pyrrolidine (V). The debenzylation of (V) with ammonium formate over Pd/C in methanol affords 3-(4-fluorophenyl)pyrrolidine (VI), which is finally condensed with 2-(4-bromobutyl)-1,2-benzoisothiazol-3-one S,S-dioxide (VII) by means of triethylamine in acetonitrile.

1 Lee, C.-H.; Ahn, K.H.; Lee, S.J.; Park, T.K.; Hong, C.Y.; N-Substituted-3-arylpyrrolidines: Potent and selective ligands at serotonin 1A receptor. Bioorg Med Chem Lett 1999, 9, 10, 1379.
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) 22746 1-benzyl-3-pyrrolidinol C11H15NO 详情 详情
(II) 30988 1-benzyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]pyrrolidine C14H21NOS 详情 详情
(III) 30989 1-benzyl-3-pyrrolidinyl 4-methylbenzenesulfonate C18H21NO3S 详情 详情
(V) 30992 1-benzyl-3-(4-fluorophenyl)pyrrolidine C17H18FN 详情 详情
(VI) 30993 3-(4-fluorophenyl)pyrrolidine C10H12FN 详情 详情
(VII) 17043 2-(4-bromobutyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione C11H12BrNO3S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

Treatment of 1-benzyl-3-hydroxypyrrolidine (I) with methanesulfonyl chloride in the presence of DMAP and Et3N affords mesylate (II). Subsequent displacement of the mesylate group of (II) with the diarylcuprate reagent generated from 4-fluorophenyllithium (III) and cuprous bromide gives the 3-aryl pyrrolidine (IV). The N-benzyl group of (IV) is then removed by transfer hydrogenolysis with ammonium formate and Pd/C, yielding the secondary amine (V). This is finally alkylated with 2-(4-bromobutyl)-3-oxo-1,2-benzisothiazole 1,1-dioxide (VI) in the presence of Et3N in refluxing acetonitrile.

1 Lee, C.-H.; Ahn, K.H.; Lee, S.J.; Park, T.K.; Hong, C.Y.; N-Substituted-3-arylpyrrolidines: Potent and selective ligands at serotonin 1A receptor. Bioorg Med Chem Lett 1999, 9, 10, 1379.
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) 22746 1-benzyl-3-pyrrolidinol C11H15NO 详情 详情
(II) 62833 1-benzyl-3-pyrrolidinyl methanesulfonate C12H17NO3S 详情 详情
(III) 62834 (4-fluorophenyl)lithium C6H4FLi 详情 详情
(IV) 30992 1-benzyl-3-(4-fluorophenyl)pyrrolidine C17H18FN 详情 详情
(V) 30993 3-(4-fluorophenyl)pyrrolidine C10H12FN 详情 详情
(VI) 17043 2-(4-bromobutyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione C11H12BrNO3S 详情 详情
Extended Information