(1S,2R)-2-phenylcyclohexyl 4-methoxybenzenesulfinate -Drug Synthesis Database

【结构式】

【分子编号】23170

【品名】(1S,2R)-2-phenylcyclohexyl 4-methoxybenzenesulfinate

【CA登记号】

【分子式】C₁₉H₂₂O₃S

【分子量】330.44788

【元素组成】C 69.06% H 6.71% O 14.53% S 9.7%

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：(IV)

Oxidation of disulfide (I) with sulfuryl chloride in AcOH at -20 C afforded (4-methoxyphenyl)sulfinyl chloride (II), which was condensed with (1R,2S)-2-phenylcyclohexanol to provide sulfinate (IV) as a single diastereomer. Subsequent condensation with the Grignard reagent (V) produced the chiral sulfoxide (VI). The diethyl acetal of (VI) was then hydrolyzed to the corresponding benzaldehyde (VII) using p-TsOH in THF-H2O. Finally, condensation of (VII) with N-cyclohexylpiperazine (VIII) using titanium tetraisopropoxide, followed by addition of diethylaluminum cyanide, furnished the target piperazinylacetonitrile.

参考文献中间体

合成目标

【1】 Lowe, D.B.; Guzik, H.S.; Kozlowski, J.A.; et al.; Diphenyl sulfoxides as selective antagonists of the muscarinic M2 receptor. Bioorg Med Chem Lett 2000, 10, 20, 2255.
【2】 Lowe, D.; Chang, W.; Kozlowski, J.; Berger, J.G.; McQuade, R.; Barnett, A.; Scherlock, M.; Tom, W.; Dugar, S.; Chen, L.-Y.; Clader, J.W.; Chackalamannil, S. (Schering Corp.); Benzylpiperidines and piperazines as muscarinic an. EP 0811002; JP 1999501014; US 5883096; WO 9626196 .

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)	23167	1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene; bis(4-methoxyphenyl) disulfide	5335-87-5	C₁₄H₁₄O₂S₂	详情	详情
(II)	23168	4-methoxybenzenesulfinyl chloride		C₇H₇ClO₂S	详情	详情
(III)	23169	(1S,2R)-2-phenylcyclohexanol		C₁₂H₁₆O	详情	详情
(IV)	23170	(1S,2R)-2-phenylcyclohexyl 4-methoxybenzenesulfinate		C₁₉H₂₂O₃S	详情	详情
(V)	23171	bromo[4-(diethoxymethyl)phenyl]magnesium		C₁₁H₁₅BrMgO₂	详情	详情
(VI)	23172	[4-(diethoxymethyl)phenyl](4-methoxyphenyl)oxo-lambda(4)-sulfane; 4-(diethoxymethyl)phenyl 4-methoxyphenyl sulfoxide		C₁₈H₂₂O₄S	详情	详情
(VII)	23173	4-[(4-methoxyphenyl)sulfinyl]benzaldehyde		C₁₄H₁₂O₃S	详情	详情
(VIII)	23174	1-cyclohexylpiperazine	17766-28-8	C₁₀H₂₀N₂	详情	详情

Extended Information