(3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide -Drug Synthesis Database

【结构式】

【分子编号】53280

【品名】(3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide

【CA登记号】n/a

【分子式】C₁₅H₂₃NS

【分子量】249.42036

【元素组成】C 72.23% H 9.29% N 5.62% S 12.86%

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 reaction of 3-(1-propylpiperidin-3(S)-yl)phenol (I) with trifluoromethanesulfonic anhydride gives the triflate (II), which is treated with triisopropylsilylthiol sodium salt and Pd(PPh3)4 to yield the sill sulfanyl compound (III). The desilylation of (III) with HCl in methanol affords the thiophenol (IV), which is methylated with 14C-labeled methyl iodide and TEA in dichloromethane, providing the methylsulfanyl derivative (V). Finally, this compound is oxidized to the target sulfone with MCPBA and trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Chaudhary, A.G.; McGrath, J.P.; Improved synthesis of stable isotope labeled and carbon-14 labeled (S)-(-)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine hydrochloride; (-)-OSU-6162. J Label Compd Radiopharm 2000, 43, 7, 683.

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)	43381	3-[(3S)-1-propylpiperidinyl]phenol		C₁₄H₂₁NO	详情	详情
(II)	43382	3-[(3S)-1-propylpiperidinyl]phenyl trifluoromethanesulfonate		C₁₅H₂₀F₃NO₃S	详情	详情
(III)	43392	3-[(3S)-1-propylpiperidinyl]phenyl triisopropylsilyl sulfide; (3S)-1-propyl-3-[3-[(triisopropylsilyl)sulfanyl]phenyl]piperidine		C₂₃H₄₁NSSi	详情	详情
(IV)	43393	3-[(3S)-1-propylpiperidinyl]phenylhydrosulfide; 3-[(3S)-1-propylpiperidinyl]benzenethiol		C₁₄H₂₁NS	详情	详情
(V)	43386	(3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide		C₁₅H₂₃NS	详情	详情
(V)	45318	(3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide		C₁₅H₂₃NS	详情	详情
(V)	53280	(3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide	n/a	C₁₅H₂₃NS	详情	详情

Extended Information