(1R)-3-oxocyclohexanecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】54946

【品名】(1R)-3-oxocyclohexanecarboxylic acid

【CA登记号】

【分子式】C₇H₁₀O₃

【分子量】142.1546

【元素组成】C 59.14% H 7.09% O 33.76%

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：(XV)

The analogous asymmetric synthesis starting from the (R)-enantiomer of 3-oxocyclohexanecarboxylic acid (XV) was also reported. The chiral (R)-keto acid (XV), prepared by resolution of the racemic acid (XII) with brucine, was coupled with tetrahydropyridine (V) to give keto amide (XVI). Protection as the ethylene ketal (XVII), followed by amide reduction and acidic ketal hydrolysis, furnished the (R)-amino ketone (XVIII). This was converted into the title compound by addition of phenylmagnesium bromide, followed by acidic dehydration and separation of isomers as in Scheme 19758501a.

参考文献中间体

合成目标

【1】 Wright, J.L.; et al.; The discovery and structure-activity relationships of 1,2,3, 6-tetrahydro-4-phenyl-1-[(arylcyclohexenyl)alkyl]pyridines. Dopamine autoreceptor agonists and potential antipsychotic agents. J Med Chem 1994, 37, 21, 3523.

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)	13002	4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine	10338-69-9	C₁₁H₁₃N	详情	详情
(XII)	54943	3-oxocyclohexanecarboxylic acid		C₇H₁₀O₃	详情	详情
(XIV)	54948	(7R)-1,4-dioxaspiro[4.5]dec-7-yl[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone		C₂₀H₂₅NO₃	详情	详情
(XV)	54946	(1R)-3-oxocyclohexanecarboxylic acid		C₇H₁₀O₃	详情	详情
(XVI)	54947	(3R)-3-{[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]carbonyl}cyclohexanone		C₁₈H₂₁NO₂	详情	详情
(XVII)	54948	(7R)-1,4-dioxaspiro[4.5]dec-7-yl[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methanone		C₂₀H₂₅NO₃	详情	详情
(XVIII)	54949	(3R)-3-{[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]methyl}cyclohexanone		C₁₈H₂₃NO	详情	详情

Extended Information