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【结 构 式】

【分子编号】54059

【品名】1-(4-sulfanylphenyl)-1-ethanone

【CA登记号】n/a

【 分 子 式 】C8H8OS

【 分 子 量 】152.21692

【元素组成】C 63.13% H 5.3% O 10.51% S 21.07%

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:(II)

The reaction of 4-fluoroacetophenone (I) with sodium hydrogensulfide in hot DMF gives 4-sulfanylacetophenone (II), which is condensed with 5-iodo-1,3-benzodioxole (III) by means of CuI and K2CO3 in hot DMF to yield the thioether (IV). The oxidation of (IV) with MCPBA in dichloroethane affords the sulfone (V), which is enantioselectively reduced by means of BH3/SMe2 and Corey's oxoborolidine catalyst in THF to provide the chiral (R)-alcohol (VI). The reaction of (VI) with Ms-Cl in dichloromethane gives the mesylate (VII), which is condensed with the monoprotected 2(R)-methylpiperazine (VIII) by means of tetramethylpiperidine (TMP) in refluxing acetonitrile to yield the expected benzylic (S)-methyl compound (IX). The elimination of the Boc protecting group of (IX) with refluxing 6N HCl affords the piperazine derivative (X), which is reductocondensed with 1-(Boc)piperidin-4-one (XI) by means of NaBH(OAc)3 to provide adduct (XII). Elimination of the Boc protecting group of (XII) as before gives the piperidine derivative (XIII), which is finally sulfonated with ethylsulfonyl chloride and TEA to provide the target ethylsufonyl piperidine.

1 Kozlowski, J.A.; Zhou, G.; Tagat, J.R.; et al.; Substituted 2-(R)-methyl piperazines as muscarinic M2 selective ligands. Bioorg Med Chem Lett 2002, 12, 5, 791.
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) 37684 1-(4-fluorophenyl)-1-ethanone 403-42-9 C8H7FO 详情 详情
(II) 54059 1-(4-sulfanylphenyl)-1-ethanone n/a C8H8OS 详情 详情
(III) 54060 1-Iodo-3,4-methylenedioxybenzene 5876-51-7 C7H5IO2 详情 详情
(IV) 54061 1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]-1-ethanone n/a C15H12O5S 详情 详情
(V) 50643 1-[4-(1,3-benzodioxol-5-ylsulfanyl)phenyl]-1-ethanone C15H12O3S 详情 详情
(VI) 50645 (1R)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]-1-ethanol C15H14O5S 详情 详情
(VII) 50646 (1R)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl methanesulfonate C16H16O7S2 详情 详情
(VIII) 51868 tert-butyl (3S)-3-methyl-1-piperazinecarboxylate C10H20N2O2 详情 详情
(IX) 54062 tert-butyl (3R)-4-{(1S)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl}-3-methyl-1-piperazinecarboxylate n/a C25H32N2O6S 详情 详情
(X) 50649 (2R)-1-[(1S)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl]-2-methylpiperazine; 1,3-benzodioxol-5-yl 4-[(1S)-1-[(2R)-2-methylpiperazinyl]ethyl]phenyl sulfone C20H24N2O4S 详情 详情
(XI) 18620 tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone 79099-07-3 C10H17NO3 详情 详情
(XII) 54063 tert-butyl 4-((3R)-4-{(1S)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl}-3-methylpiperazinyl)-1-piperidinecarboxylate n/a C30H41N3O6S 详情 详情
(XIII) 54064 (2R)-1-{(1S)-1-[4-(1,3-benzodioxol-5-ylsulfonyl)phenyl]ethyl}-2-methyl-4-(4-piperidinyl)piperazine; 1,3-benzodioxol-5-yl 4-{(1S)-1-[(2R)-2-methyl-4-(4-piperidinyl)piperazinyl]ethyl}phenyl sulfone n/a C25H33N3O4S 详情 详情
(XIV) 54065 Ethanesulfonyl chloride; Ethylsulfonyl chloride 594-44-5 C2H5ClO2S 详情 详情
Extended Information