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【结 构 式】 
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【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% |
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 . |