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【结 构 式】

【分子编号】29275

【品名】3,3-diphenyl-1-propanamine

【CA登记号】5586-73-2

【 分 子 式 】C15H17N

【 分 子 量 】211.30672

【元素组成】C 85.26% H 8.11% N 6.63%

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:(III)

Treatment of (Boc)-beta-methyltryptophan (I) with SOCl2 and MeOH produced beta-methyltryptophan methyl ester (II). 3,3-Diphenylpropylamine (III) was protected with Boc2O and then alkylated with allyl bromide in the presence of potassium hexamethyldisilazide to afford (IV). Further ozonization of the allyl double bond of (IV) generated the aminoaldehyde (V). Amino ester (II) was reductively alkylated with aldehyde (V) in the presence of NaBH3CN to yield the protected diamine (VI). After acid deprotection of the Boc group of (VI), the resulting diamine (VII) was converted to imidazolinone (VIII) upon treatment with phosgene and diisopropylethylamine. Subsequent hydrolysis of the methyl ester of (VIII) gave carboxylic acid (IX).

1 Marino, D.; Pan, Y.; Pasternak, A.; et al.; Potent, orally bioavailable somatostatin agonists: Good absorption achieved by urea backbone cyclization. Bioorg Med Chem Lett 1999, 9, 3, 491.
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) 28255 (2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)butyric acid C17H22N2O4 详情 详情
(II) 29274 methyl (2R,3S)-2-amino-3-(1H-indol-3-yl)butanoate C13H16N2O2 详情 详情
(III) 29275 3,3-diphenyl-1-propanamine 5586-73-2 C15H17N 详情 详情
(IV) 29276 tert-butyl allyl(3,3-diphenylpropyl)carbamate C23H29NO2 详情 详情
(V) 29277 tert-butyl 3,3-diphenylpropyl(2-oxoethyl)carbamate C22H27NO3 详情 详情
(VI) 29278 methyl (2R,3S)-2-([2-[(tert-butoxycarbonyl)(3,3-diphenylpropyl)amino]ethyl]amino)-3-(1H-indol-3-yl)butanoate C35H43N3O4 详情 详情
(VII) 29279 methyl (2R,3S)-2-([2-[(3,3-diphenylpropyl)amino]ethyl]amino)-3-(1H-indol-3-yl)butanoate C30H35N3O2 详情 详情
(VIII) 29280 methyl (2R,3S)-2-[3-(3,3-diphenylpropyl)-2-oxo-1-imidazolidinyl]-3-(1H-indol-3-yl)butanoate C31H33N3O3 详情 详情
(IX) 29281 (2R,3S)-2-[3-(3,3-diphenylpropyl)-2-oxo-1-imidazolidinyl]-3-(1H-indol-3-yl)butyric acid C30H31N3O3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The title compound is prepared by alkylation of 3,3-diphenylpropylamine (I) with bromoacetamide (II) in the presence of K2CO3 in acetonitrile (1).

1 Ognyanov, V.I.; Borden, L.; Bell, S.C.; Zhang, J. (NPS Allelix Corp.); Pharmaceutical for treatment of neurological and neuropsychiatric disorders. EP 1014966; JP 2002515037; US 6191165; WO 9745115 .
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) 29275 3,3-diphenyl-1-propanamine 5586-73-2 C15H17N 详情 详情
(II) 38747 2-bromoacetamide 683-57-8 C2H4BrNO 详情 详情
Extended Information