1,1-Diphenylethyl cyanide; alpha,alpha-Diphenylpropionitrile; 2,2-Diphenylpropionitrile -Drug Synthesis Database

【结构式】

【分子编号】48521

【品名】1,1-Diphenylethyl cyanide; alpha,alpha-Diphenylpropionitrile; 2,2-Diphenylpropionitrile

【CA登记号】5558-67-8

【分子式】C₁₅H₁₃N

【分子量】207.27496

【元素组成】C 86.92% H 6.32% N 6.76%

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：(I)

Reduction of 2,2-diphenylpropionitrile (I) with LiAlH4 in Et2O produced aldehyde (II), which was further converted to cyanohydrin (III) upon treatment with KCN and p-toluenesulfonic acid. The required alpha-hydroxy ester (V) was obtained either by sequential hydrolysis of (III) to amide (IV) and then to ester (V) under acidic conditions or by direct conversion of nitrile (III) to ester (V) with boiling hydroalcoholic HCl. Subsequent saponification of the ester group of (V) with LiOH provided hydroxy acid (VI). This was finally condensed with 4,6-dimethyl-2-chloropyrimidine (VII) in the presence of NaH to give the racemic pyrimidinyl ether.

参考文献中间体

合成目标

【1】 Klinge, D.; Amberg, W.; Baumann, E.; Kling, A.; Riechers, H.; Unger, L.; Raschack, M.; Hergenroder, S.; Schult, S. (BASF AG); Novel alpha-hydroxylic acid derivs., their production and use. DE 19614533; EP 0892787; JP 2000508326; WO 9738981 .

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)	48521	1,1-Diphenylethyl cyanide; alpha,alpha-Diphenylpropionitrile; 2,2-Diphenylpropionitrile	5558-67-8	C₁₅H₁₃N	详情	详情
(II)	48522	2,2-diphenylpropanal		C₁₅H₁₄O	详情	详情
(III)	48523	2-hydroxy-3,3-diphenylbutanenitrile		C₁₆H₁₅NO	详情	详情
(IV)	48524	2-hydroxy-3,3-diphenylbutanamide		C₁₆H₁₇NO₂	详情	详情
(V)	48525	ethyl 2-hydroxy-3,3-diphenylbutanoate		C₁₈H₂₀O₃	详情	详情
(VI)	48526	2-hydroxy-3,3-diphenylbutyric acid		C₁₆H₁₆O₃	详情	详情
(VII)	48527	2-chloro-4,6-dimethylpyrimidine		C₆H₇ClN₂	详情	详情

Extended Information