3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl trifluoromethanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】62830

【品名】3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl trifluoromethanesulfonate

【CA登记号】

【分子式】C₁₇H₁₇Cl₂F₃O₃S

【分子量】429.2867896

【元素组成】C 47.56% H 3.99% Cl 16.52% F 13.28% O 11.18% S 7.47%

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：(V)

Preparation of the intermediate aryl triflate (V) is shown is Scheme 29890101a. The dilithiated derivative of 4-bromo-3,5-dichlorophenol (I) is condensed with 2-adamantanone (II) to produce the carbinol adduct (III). Reduction of the tertiary alcohol of (III) by means of concentrated HI in boiling AcOH leads to the adamantanyl phenol (IV). This is then reacted with trifluoromethanesulfonic anhydride in cold pyridine to yield sulfonate (V).

参考文献中间体

合成目标

【1】 Paul, R.; Boigegrain, R.; Nisato, D.; Casellas, P.; Herbert, J.M.; Bourrie, B.; Bourrie, M.; Lair, P.; Vernieres, J.C. (Sanofi-Synthélabo); Benzene derivs., preparation method and pharmaceutical compsns. containing same. EP 1192122; FR 2794742; JP 2003502306; US 6482986; WO 0076953 .

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)	62827	4-bromo-3,5-dichlorophenol		C₆H₃BrCl₂O	详情	详情
(II)	40404	2-adamantanone	700-58-3	C₁₀H₁₄O	详情	详情
(III)	62828	2-(2,6-dichloro-4-hydroxyphenyl)tricyclo[3.3.1.1^3,7]decan-2-ol		C₁₆H₁₈Cl₂O₂	详情	详情
(IV)	62829	3,5-dichloro-4-tricyclo[3.3.1.1^3,7]dec-2-ylphenol		C₁₆H₁₈Cl₂O	详情	详情
(V)	62830	3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl trifluoromethanesulfonate		C₁₇H₁₇Cl₂F₃O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Alkylation of cyclohexyl ethylamine (VI) with propargyl bromide (VII) gives the tertiary amine (VIII). Then, palladium-catalyzed coupling between the propargylic amine (VIII) and aryl triflate (V) furnishes the disubstituted acetylene derivative (IX). Finally, semihydrogenation of the triple bond of (IX) in the presence of cyclohexene and Lindlar catalyst gives rise to the target cis-olefin.

参考文献中间体

合成目标

【1】 Paul, R.; Boigegrain, R.; Nisato, D.; Casellas, P.; Herbert, J.M.; Bourrie, B.; Bourrie, M.; Lair, P.; Vernieres, J.C. (Sanofi-Synthélabo); Benzene derivs., preparation method and pharmaceutical compsns. containing same. EP 1192122; FR 2794742; JP 2003502306; US 6482986; WO 0076953 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	62830	3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl trifluoromethanesulfonate		C₁₇H₁₇Cl₂F₃O₃S	详情	详情
(VI)	59245	N-Ethylcyclohexanamine; N-Ethylcyclohexylamine; Vulkacit HX	5459-93-8	C₈H₁₇N	详情	详情
(VII)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(VIII)	62831	N-ethyl-N-(2-propynyl)cyclohexanamine; N-cyclohexyl-N-ethyl-N-(2-propynyl)amine		C₁₁H₁₉N	详情	详情
(IX)	62832	N-[3-(3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl)-2-propynyl]-N-ethylcyclohexanamine; N-cyclohexyl-N-[3-(3,5-dichloro-4-tricyclo[3.3.1.1~3,7~]dec-2-ylphenyl)-2-propynyl]-N-ethylamine		C₂₇H₃₅Cl₂N	详情	详情

Extended Information