1-benzyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]pyrrolidine -Drug Synthesis Database

【结构式】

【分子编号】30988

【品名】1-benzyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]pyrrolidine

【CA登记号】

【分子式】C₁₄H₂₁NOS

【分子量】251.39288

【元素组成】C 66.89% H 8.42% N 5.57% O 6.36% S 12.76%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

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 diphenyl cuprate lithium (IV) yielding 1-benzyl-3-phenylpyrrolidine (V). The debenzylation of (V) with ammonium formate over Pd/C in methanol affords 3-phenylpyrrolidine (VI), which is finally condensed with 2-(4-bromobutyl)-1,2-benzoisothiazol-3-one S,S-dioxide (VII) by means of triethylamine in acetonitrile.

参考文献中间体

合成目标

【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
	13975	p-Toluenesulfonyl chloride;p-tosyl chloride;Toluene-4-sulfonyl chloride;4-Toluene sulfochloride;tosyl chloride; 4-Methylbenzenesulfonyl chloride	98-59-9	C₇H₇ClO₂S	详情	详情
(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)	30990	1-benzyl-3-phenylpyrrolidine		C₁₇H₁₉N	详情	详情
(VI)	30991	3-phenylpyrrolidine		C₁₀H₁₃N	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：(II)

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.

参考文献中间体

合成目标

【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	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

Extended Information