2-Methyl-3-(1-pyrrolidinyl)-1-[4-(trifluoromethyl)phenyl]-1-propanone -Drug Synthesis Database

【结构式】

【分子编号】13384

【品名】2-Methyl-3-(1-pyrrolidinyl)-1-[4-(trifluoromethyl)phenyl]-1-propanone

【CA登记号】

【分子式】C₁₅H₁₈F₃NO

【分子量】285.3092696

【元素组成】C 63.15% H 6.36% F 19.98% N 4.91% O 5.61%

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：(V)

The Grignard reaction of 4-(trifluoromethyl)benzaldehyde (I) with ethylmagnesium bromide in ethyl ether gives 1-[4-(trifluoromethyl)phenyl]-1-propanol (II), which is oxidized with CrO3/H2SO4 yielding 4-(trifluoromethyl)propiophenone (III). The condensation of (III) with pyrrolidine (IV) and paraformaldehyde by means of HCl in refluxing isopropanol affords racemic 2-methyl-3-(1-pyrrolidinyl)propiophenone (V), which is finally submitted to optical resolution with N-acetyl-L-phenylglycine (VI) or D-malic acid (VII) and treated with dry HCl gas.

参考文献中间体

合成目标

【1】 Kurashige, S.; Izumi, G.; Shiozawa, A.; Narita, K.; Sakitama, K.; Ishikawa, M.; Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants. Eur J Med Chem 1995, 30, 1, 85-94.
【2】 Wroblewskki, T.; Castaner, J.; Leeson, P.; Lanperisone Hydrochloride. Drugs Fut 1998, 23, 5, 485.
【3】 Shiozawa, A.; Ishikawa, M.; Sugimura, H.; Yamamoto, H.; Sakasai, T.; Ohtsuki, K.; Kurashige, S. (Nippon Kayaku Co., Ltd.); An optically active propanone deriv. and process for producing the same and use thereof. EP 0266577; JP 1989131171 .

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)	13380	4-(Trifluoromethyl)benzaldehyde; alpha,alpha,alpha-Trifluoro-p-tolualdehyde	455-19-6	C₈H₅F₃O	详情	详情
(II)	13381	1-[4-(Trifluoromethyl)phenyl]-1-propanol		C₁₀H₁₁F₃O	详情	详情
(III)	13382	1-[4-(Trifluoromethyl)phenyl]-1-propanone; 4-(Trifluoromethyl)propiophenone	711-33-1	C₁₀H₉F₃O	详情	详情
(IV)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(V)	13384	2-Methyl-3-(1-pyrrolidinyl)-1-[4-(trifluoromethyl)phenyl]-1-propanone		C₁₅H₁₈F₃NO	详情	详情
(VI)	13385	(2S)-2-(Acetamido)-2-phenylethanoic acid		C₁₀H₁₁NO₃	详情	详情

Extended Information