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【结 构 式】

【分子编号】37016

【品名】1-(6-fluoro-3,4-dihydro-2-naphthalenyl)pyrrolidine

【CA登记号】

【 分 子 式 】C14H16FN

【 分 子 量 】217.2861832

【元素组成】C 77.39% H 7.42% F 8.74% N 6.45%

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)

Condensation of 4-fluorophenylacetyl chloride (I) with ethylene in the presence of AlCl3 provided the beta-tetralone (II). After conversion of (III) into enamine (IV) upon reaction with pyrrolidine (III) in MeOH, alkylation with allyl bromide (V) afforded iminium salt (VI). Acid hydrolysis of (VI) generated the allyl tetralone (VII), which was subjected to reductive amination with ammonium acetate and sodium cyanoborohydride to produce the cis-1-allyl-2-aminotetralin (VIII) as the major isomer. Coupling of (VIII) with carboxylic acid (IX) using 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) gave amide (X), which was finally reduced to the target aminotetralin derivative with LiAlH4.

1 Lovenberg, T.W.; McNally, J.J.; Youngman, M.A.; et al.; alpha-Substituted N-(sulfonamido)alkyl-beta-aminotetralins: Potent and selective neuropeptide Y Y5 receptor antagonists. J Med Chem 2000, 43, 3, 346.
2 Reitz, A.B.; Lovenberg, T.W.; Dax, S.L.; Youngman, M.A.; McNally, J.J. (Ortho-McNeil Pharmaceutical, Inc.); N-Substd. aminotetralins as ligands for the neuropeptide Y Y5 receptor useful in the treatment of obesity and other disorders. WO 9955667 .
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) 37014 2-(4-fluorophenyl)acetyl chloride 459-04-1 C8H6ClFO 详情 详情
(II) 37015 6-fluoro-3,4-dihydro-2(1H)-naphthalenone C10H9FO 详情 详情
(III) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(IV) 37016 1-(6-fluoro-3,4-dihydro-2-naphthalenyl)pyrrolidine C14H16FN 详情 详情
(V) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(VI) 37017 1-[1-allyl-6-fluoro-3,4-dihydro-2(1H)-naphthalenylidene]pyrrolidinium bromide C17H21BrFN 详情 详情
(VII) 37018 1-allyl-6-fluoro-3,4-dihydro-2(1H)-naphthalenone C13H13FO 详情 详情
(VIII) 37019 (1S,2R)-1-allyl-6-fluoro-1,2,3,4-tetrahydro-2-naphthalenamine; (1S,2R)-1-allyl-6-fluoro-1,2,3,4-tetrahydro-2-naphthalenylamine C13H16FN 详情 详情
(IX) 37020 4-[[(phenylsulfonyl)amino]methyl]cyclohexanecarboxylic acid C14H19NO4S 详情 详情
(X) 37021 N-[(1S,2R)-1-allyl-6-fluoro-1,2,3,4-tetrahydro-2-naphthalenyl]-4-[[(phenylsulfonyl)amino]methyl]cyclohexanecarboxamide C27H33FN2O3S 详情 详情
Extended Information