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【结 构 式】

【分子编号】64723

【品名】1,1-dimethylethyl 3-(trimethylstannanyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

【CA登记号】

【 分 子 式 】C15H27NO2Sn

【 分 子 量 】372.09492

【元素组成】C 48.42% H 7.31% N 3.76% O 8.6% Sn 31.9%

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:(V)

Demethylation of tropinone (I) by means of 1-chloroethyl chloroformate, followed by protection of the resultant secondary amine (II) with di-tert-butyl dicarbonate, leads to the N-Boc derivative (III). Treatment of the potassium enolate of (III) with N-phenyl trifluoromethanesulfonimide produces the vinyl triflate (IV), which is then converted to the stannyl derivative (V) upon treatment with hexamethylditin and palladium catalyst. Stille coupling of (V) with ethyl 2-bromobenzoate (VI) affords (VII). After catalytic double bond hydrogenation of (VII), the resultant mixture of diastereoisomers is separated by recrystallization from hexane/ethyl acetate to give (VIII). The N-Boc protecting group of (VIII) is cleaved with HCl in dioxane to yield amine (IX), which is then coupled with N-Boc-D-benzylalanine (X) to furnish amide (XI). Subsequent acidic Boc-group cleavage gives rise to the amine (XII).

1 Lu, Z.; Tata, J.R.; Cheng, K.; Wei, L.; Chan, W.W.-S.; Butler, B.; Schleim, K.D.; Jacks, T.M.; Hickey, G.; Patchett, A.A.; Substituted bridged phenyl piperidines: Orally active growth hormone secretagogues. Bioorg Med Chem Lett 2003, 13, 10, 1817.
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) 16443 (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-one C8H13NO 详情 详情
(II) 64720 8-azabicyclo[3.2.1]octan-3-one C7H11NO 详情 详情
(III) 64721 1,1-dimethylethyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate C12H19NO3 详情 详情
(IV) 64722 1,1-dimethylethyl 3-{[(trifluoromethyl)sulfonyl]oxy}-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate C13H18F3NO5S 详情 详情
(V) 64723 1,1-dimethylethyl 3-(trimethylstannanyl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate C15H27NO2Sn 详情 详情
(VI) 58367 ethyl 2-bromobenzoate; 2-Bromobenzoic acid ethyl ester 6091-64-1 C9H9BrO2 详情 详情
(VII) 64724 1,1-dimethylethyl 3-{2-[(ethyloxy)carbonyl]phenyl}-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate C21H27NO4 详情 详情
(VIII) 64725 1,1-dimethylethyl 3-{2-[(ethyloxy)carbonyl]phenyl}-8-azabicyclo[3.2.1]octane-8-carboxylate C21H29NO4 详情 详情
(IX) 64726 ethyl 2-(8-azabicyclo[3.2.1]oct-3-yl)benzoate C16H21NO2 详情 详情
(X) 52886 Boc-(-)-alpha-amino-4-phenylbutyric acid; Boc-D-Homophenylalanine 82732-07-8 C15H21NO4 详情 详情
(XI) 64727 ethyl 2-{8-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-phenylbutanoyl]-8-azabicyclo[3.2.1]oct-3-yl}benzoate C31H40N2O5 详情 详情
(XII) 64728 ethyl 2-[8-(2-amino-4-phenylbutanoyl)-8-azabicyclo[3.2.1]oct-3-yl]benzoate C26H32N2O3 详情 详情
Extended Information