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【结 构 式】

【分子编号】65698

【品名】1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide

【CA登记号】768-90-1

【 分 子 式 】C10H15Br

【 分 子 量 】215.1331

【元素组成】C 55.83% H 7.03% Br 37.14%

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:(XXII)

The preparation of the hydroxylated adamantane (IV) is shown in Scheme 3. 1-Adamantyl bromide (XXII) is condensed with 1,1,2-tris(trimethylsilyloxy)ethylene (XXIII) by means of ZnCl2 in CH2Cl2 to afford the adamantylglycolic acid (XXIV), which is esterified to (XXV) utilizing a solution of acetyl chloride in MeOH. After Swern oxidation of (XXV) to the corresponding keto ester (XXVI), hydroxylation of the adamantane ring by means of HNO3/H2SO4 provides (XXVII). Alkaline hydrolysis of ester (XXVII) leads to the oxoacetic acid (XXVIII), which is converted to the target (S)-amino acid (IV) by reductive amination with phenylalanine dehydrogenase (3).

3 Politino, M., Cadin, M.M., Skonezny, P.M., Chen, J.G. (Bristol-Myers Squibb Co.). EP 1737970, JP 2007532137, WO 2005106011.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 65681 (S)-(3-hydroxyadamantyl)glycine   C12H19NO3 详情 详情
(XXII) 65698 1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide 768-90-1 C10H15Br 详情 详情
(XXIII) 14534 2,2,7,7-tetramethyl-4-[(trimethylsilyl)oxy]-3,6-dioxa-2,7-disila-4-octene; 1,2-bis[(trimethylsilyl)oxy]vinyl trimethylsilyl ether; TRIS(TRIMETHYLSILYLOXY)ETHYLENE 69097-20-7 C11H28O3Si3 详情 详情
(XXIV) 65699     C12H18O3 详情 详情
(XXV) 65700     C13H20O3 详情 详情
(XXVI) 65701     C13H18O3 详情 详情
(XXVII) 65702 Methyl 2-(3-Hydroxy-1-adamantyl)-2-oxoacetate   C13H18O4 详情 详情
(XXVIII) 65703 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid; 3-Hydroxy-alpha-oxotricyclo[3.3.1.1(3,7)]decane-1-acetic acid; 709031-28-7 C12H16O4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

 

中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 65680 N-Boc-(S)-(3-hydroxyadamantyl)glycine   C17H28NO5 详情 详情
(I) 62440 methyl 2,2,2-trichloroacetate 598-99-2 C3H3Cl3O2 详情 详情
(II) 65698 1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide 768-90-1 C10H15Br 详情 详情
(III) 67428 methyl 2-(adamantan-1-yl)-2,2-dichloroacetate   C13H18Cl2O2 详情 详情
(IV) 67429 methyl 2,2-dichloro-2-(3-hydroxyadamantan-1-yl)acetate   C13H18Cl2O3 详情 详情
(V) 67430 2,2-dichloro-2-(3-hydroxyadamantan-1-yl)acetic acid   C12H16Cl2O3 详情 详情
(VI) 65703 2-(3-Hydroxy-1-adamantyl)-2-oxoacetic acid; 3-Hydroxy-alpha-oxotricyclo[3.3.1.1(3,7)]decane-1-acetic acid; 709031-28-7 C12H16O4 详情 详情
(VII) 65681 (S)-(3-hydroxyadamantyl)glycine   C12H19NO3 详情 详情
(IX) 67427 ((2,2-dichloro-1-methoxyvinyl)oxy)trimethylsilane   C6H12Cl2O2Si 详情 详情
Extended Information