1-Bromoadamantane; 1-Bromotricyclo[3.3.1.1(3,7)]decane; 1-Adamantyl bromide -Drug Synthesis Database

【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 合成路线2

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).

参考文献中间体

合成目标

【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)

参考文献中间体

合成目标

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