ethyl 4-(benzhydryloxy)tetrahydro-1(2H)-pyridinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】12080

【品名】ethyl 4-(benzhydryloxy)tetrahydro-1(2H)-pyridinecarboxylate

【CA登记号】

【分子式】C₂₁H₂₅NO₃

【分子量】339.43444

【元素组成】C 74.31% H 7.42% N 4.13% O 14.14%

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：(VII)

Synthesis of intermediate (X): 4-Hydroxypiperidine (V) is protected with ethyl chloroformate to give (VI), which is then condensed with bromodiphenylmethane in the presence of sodium carbonate yielding (VII). AIkali hydrolysis of (VII) gives (VIII), which is then treated with N-(2-bromoethyl)phthalimide to yield (IX). (IX) is then deprotected by a treatment of 80% hydrazine hydrate, producing (X).

参考文献中间体

合成目标

【1】 Tasaka, K.; TMK-688. Drugs Fut 1988, 13, 12, 1056.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	37025	2-(2-bromoethyl)-1H-isoindole-1,3(2H)-dione	574-98-1	C₁₀H₈BrNO₂	详情	详情
(IIb)	12079	Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide	776-74-9	C₁₃H₁₁Br	详情	详情
(V)	12076	4-Piperidinol; 4-Hydroxypiperidine	5382-16-1	C₅H₁₁NO	详情	详情
(VI)	22709	ethyl 4-hydroxy-1-piperidinecarboxylate		C₈H₁₅NO₃	详情	详情
(VII)	12080	ethyl 4-(benzhydryloxy)tetrahydro-1(2H)-pyridinecarboxylate		C₂₁H₂₅NO₃	详情	详情
(VIII)	12081	4-(Benzhydryloxy)piperidine; Benzhydryl 4-piperidinyl ether		C₁₈H₂₁NO	详情	详情
(IX)	22713	2-[2-[4-(benzhydryloxy)-1-piperidinyl]ethyl]-1H-isoindole-1,3(2H)-dione		C₂₈H₂₈N₂O₃	详情	详情
(X)	22707	2-[4-(benzhydryloxy)-1-piperidinyl]ethylamine; 2-[4-(benzhydryloxy)-1-piperidinyl]-1-ethanamine		C₂₀H₂₆N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

This compound can be obtained by two related routes: 1) Condensation of 4-hydroxypiperidine (I) with p-tert-butyl-omega-chlorobutyrophenone (II) in hot methyl isobutyl ketone in presence of sodium bicarbonate gives 1-[3-(4-tert-butylbenzoyl)propyl]-4-hydroxypiperidine (III), which reacts with diphenylmethyl bromide (IV) in methyl isobutyl ketone to give ebastine. 2) 4-Diphenylmethoxypiperidine (VI), obtained by alkaline hydrolysis of 1-ethoxycarbonyl-4-diphenyl-methoxypiperidine (V) was reacted with p-tert-butyl-omega-chlorobutyrophenone (II) to give ebastine.

参考文献中间体

合成目标

【1】 Spickett, R.G.W.; Moragues, J.; Prieto, J.; Vega, A. (Fordonal S.A.); Piperidine derivs. EP 0134124B; US 4550116 .
【2】 Moragues, J.; Roberts, D.J.; EBASTINE. Drugs Fut 1990, 15, 7, 674.

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)	12076	4-Piperidinol; 4-Hydroxypiperidine	5382-16-1	C₅H₁₁NO	详情	详情
(II)	12077	4-Chloro-1-[4-(1,1-dimethylethyl)phenyl]-1-butanone; 1-[4-(tert-Butyl)phenyl]-4-chloro-1-butanone; 4'-tert-Butyl-4-chlorobutyrophenone	43076-61-5	C₁₄H₁₉ClO	详情	详情
(III)	12078	1-[4-(tert-Butyl)phenyl]-4-(4-hydroxypiperidino)-1-butanone		C₁₉H₂₉NO₂	详情	详情
(IV)	12079	Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide	776-74-9	C₁₃H₁₁Br	详情	详情
(V)	12080	ethyl 4-(benzhydryloxy)tetrahydro-1(2H)-pyridinecarboxylate		C₂₁H₂₅NO₃	详情	详情
(VI)	12081	4-(Benzhydryloxy)piperidine; Benzhydryl 4-piperidinyl ether		C₁₈H₂₁NO	详情	详情

Extended Information