2-fluoro-5,6-dimethoxy-2-(4-piperidinylmethyl)-1-indanone -Drug Synthesis Database

【结构式】

【分子编号】57513

【品名】2-fluoro-5,6-dimethoxy-2-(4-piperidinylmethyl)-1-indanone

【CA登记号】

【分子式】C₁₇H₂₂FNO₃

【分子量】307.3650232

【元素组成】C 66.43% H 7.21% F 6.18% N 4.56% O 15.62%

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 title compound is also prepared by a related method. Indanone (I) is fluorinated by means of N-fluorobenzenesulfonimide in the presence of lithium hexamethyldisilazide, to afford the corresponding fluoro ketone (II). Subsequent dealkylation of the N-benzyl group of (II) is accomplished by treatment with 1-chloroethyl chloroformate, to produce the intermediate carbamate (III), which is then decarboxylated to the secondary amine (IV) in boiling MeOH. Finally, piperidine (IV) is reductively alkylated with 3-fluorobenzaldehyde (V) in the presence of NaBH(OAc)3.

参考文献中间体

合成目标

【1】 Takeuchi, Y.; Yamanishi, Y.; Sugimoto, H.; Suzuki, N.; Iimura, Y.; Kawakami, Y.; Inoue, A.; Kuriya, Y.; Kosasa, T.; Recent advances in the study of acetylcholinesterase inhibitor "donepezil" (1): Synthesis and structure-activity relationships of fluorine-introduced donepezil and related compounds. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 67.

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)	57510	2-[(1-benzyl-4-piperidinyl)methyl]-5,6-dimethoxy-1-indanone		C₂₄H₂₉NO₃	详情	详情
(II)	57511	2-[(1-benzyl-4-piperidinyl)methyl]-2-fluoro-5,6-dimethoxy-1-indanone		C₂₄H₂₈FNO₃	详情	详情
(III)	57512	1-chloroethyl 4-[(2-fluoro-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl]-1-piperidinecarboxylate		C₂₀H₂₅ClFNO₅	详情	详情
(IV)	57513	2-fluoro-5,6-dimethoxy-2-(4-piperidinylmethyl)-1-indanone		C₁₇H₂₂FNO₃	详情	详情
(V)	18887	3-Fluorobenzaldehyde	456-48-4	C₇H₅FO	详情	详情

Extended Information