4-{[(4-fluorophenyl)imino]methyl}phenol -Drug Synthesis Database

【结构式】

【分子编号】53481

【品名】4-{[(4-fluorophenyl)imino]methyl}phenol

【CA登记号】3382-63-6

【分子式】C₁₃H₁₀FNO

【分子量】215.2269432

【元素组成】C 72.55% H 4.68% F 8.83% N 6.51% O 7.43%

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：(III)

The enantioselective reduction of the oxazolidinone (I) with BH3/SMe2 and a chiral borinated catalyst gives the (S)-alcohol (II), which is condensed with the labeled imine (III) (prepared by reaction of 4-fluoroaniline (IV) and 13C-labeled 4-hydroxybenzaldehyde (V)) by means of TiCl4 in dichloromethane to yield the silylated adduct (VI) (previously the reactants are silylated with Tms-Cl and DIEA). Finally, adduct (VI) is resilylated with bis(trimethylsilyl)acetamide and cyclized and desilylated by treatment with TBAF in dichloromethane to afford the target 13C-labeled SCH-58235.

参考文献中间体

合成目标

【1】 Hesk, D.; et al.; Synthesis of 3H, 14C and 13C6 labelled Sch 58235. J Label Compd Radiopharm 2002, 45, 2, 145.

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)	53476	1-(4-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-1,5-pentanedione	n/a	C₂₀H₁₈FNO₄	详情	详情
(II)	53477	(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one	n/a	C₂₀H₂₀FNO₄	详情	详情
(III)	53478		n/a	C₁₃H₁₀FNO	详情	详情
(III)	53481	4-{[(4-fluorophenyl)imino]methyl}phenol	3382-63-6	C₁₃H₁₀FNO	详情	详情
(IV)	37690	4-fluorophenylamine; 4-fluoroaniline	371-40-4	C₆H₆FN	详情	详情
(V)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(V)	53479		n/a	C₇H₆O₂	详情	详情
(VI)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid		C₁₀H₁₇NO₄	详情	详情
(VI)	53480		n/a	C₃₇H₄₀F₂N₂O₇SSi	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The enantioselective reduction of the oxazolidinone (I) with BH3/SMe2 and a chiral borinated catalyst gives the (S)-alcohol (II), which is condensed with the labeled imine (III) (prepared by reaction of 4-fluoroaniline (IV) and 14C-labeled 4-hydroxybenzaldehyde (V)) by means of TiCl4 in dichloromethane to yield the silylated adduct (VI) (previously the reactants are silylated with Tms-Cl and DIEA). Finally, adduct (VI) is resilylated with bis(trimethylsilyl)acetamide and cyclized and desilylated by treatment with TBAF in dichloromethane to afford the target 14C-labeled SCH-58235.

参考文献中间体

合成目标

【1】 Hesk, D.; et al.; Synthesis of 3H, 14C and 13C6 labelled Sch 58235. J Label Compd Radiopharm 2002, 45, 2, 145.

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)	53476	1-(4-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]-1,5-pentanedione	n/a	C₂₀H₁₈FNO₄	详情	详情
(II)	53477	(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one	n/a	C₂₀H₂₀FNO₄	详情	详情
(III)	53481	4-{[(4-fluorophenyl)imino]methyl}phenol	3382-63-6	C₁₃H₁₀FNO	详情	详情
(III)	53484		n/a	C₁₃H₁₀FNO	详情	详情
(IV)	37690	4-fluorophenylamine; 4-fluoroaniline	371-40-4	C₆H₆FN	详情	详情
(V)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(V)	53483	4-hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(VI)	53482	(1S,4R,5S)-5-(4-fluoroanilino)-1-(4-fluorophenyl)-4-{[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]carbonyl}-5-{4-[(trimethylsilyl)oxy]phenyl}pentyl methanesulfonate	n/a	C₃₇H₄₀F₂N₂O₇SSi	详情	详情
(VI)	53485		n/a	C₃₇H₄₀F₂N₂O₇SSi	详情	详情

Extended Information