2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine -Drug Synthesis Database

【结构式】

【分子编号】30079

【品名】2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine

【CA登记号】

【分子式】C₆H₁₁ClF₃N

【分子量】189.6079896

【元素组成】C 38.01% H 5.85% Cl 18.7% F 30.06% N 7.39%

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：(XIII)

Dehydroepiandrosterone (VIII) was treated with o-phenylenephosphorochloridite (V) and then with iodine to afford iodide (IX), which was reduced to (X) by means of Zn and AcOH. Bromination of (X) with CuBr2 gave bromoketone (XI), and this was hydrolyzed to hydroxyketone (XII) upon treatment with aqueous NaOH in the presence of pyridine and oxygen. Subsequent treatment of (XII) with diethyl (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded the target fluoroketone

参考文献中间体

合成目标

【1】 Lewbart, M.L.; Schwartz, A.G. (Research Corporation Technologies, Inc.); Steroids useful as anti-cancer and anti-obesity agents, a therapeutic compsn. containing them and use thereof for the preparation of a therapeutic compsn.. EP 0246650; JP 1987283993 .

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)	30072	2-chloro-1,3,2-benzodioxaphosphole	1641-40-3	C₆H₄ClO₂P	详情	详情
(VIII)	11713	Dehydroepiandrosterone;prasterone；(3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one	53-43-0	C₁₉H₂₈O₂	详情	详情
(IX)	30075	(3S,8R,9S,10R,13S,14S)-3-iodo-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₇IO	详情	详情
(X)	30076	(8R,9S,10R,13S,14S)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O	详情	详情
(XI)	30077	(8R,9S,10R,13S,14S,16R)-16-bromo-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₇BrO	详情	详情
(XII)	30078	(8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O₂	详情	详情
(XIII)	30079	2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine		C₆H₁₁ClF₃N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIII)

Dehydroepiandrosterone (VIII) was first brominated with CuBr2 to give bromoketone (XIV), which was hydrolyzed to hydroxyketone (XV). After protection of (XV) as the monoacetate (XVI), fluorination at position 16 by means of (2-chloro-1,1,2-trifluoroethyl)amine (XIII) afforded fluoroketone (XVII). Ester hydrolysis in (XVI) then gave intermediate (IV).

参考文献中间体

合成目标

【1】 Schwartz, A.G.; Lewbart, M.L.; 17-Hydroxy-steroids. US 4898694 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	30071	(3S,8R,9S,10R,13S,14S,16R)-16-fluoro-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₇FO₂	详情	详情
(VIII)	11713	Dehydroepiandrosterone;prasterone；(3S,8R,9S,10R,13S,14S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one	53-43-0	C₁₉H₂₈O₂	详情	详情
(XIII)	30079	2-chloro-N,N-diethyl-1,1,2-trifluoro-1-ethanamine; N-(2-chloro-1,1,2-trifluoroethyl)-N,N-diethylamine		C₆H₁₁ClF₃N	详情	详情
(XIV)	30080	(3S,8R,9S,10R,13S,14S,16R)-16-bromo-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₇BrO₂	详情	详情
(XV)	30081	(3S,8R,9S,10R,13S,14S,16R)-3,16-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one		C₁₉H₂₈O₃	详情	详情
(XVI)	30082	(3S,8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate		C₂₁H₃₀O₄	详情	详情
(XVII)	30083	(3S,8R,9S,10R,13S,14S,16R)-16-fluoro-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate		C₂₁H₂₉FO₃	详情	详情

Extended Information