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【结 构 式】

【分子编号】43383

【品名】methyl 3-[(3S)-1-propylpiperidinyl]benzoate

【CA登记号】

【 分 子 式 】C16H23NO2

【 分 子 量 】261.36416

【元素组成】C 73.53% H 8.87% N 5.36% O 12.24%

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:(III)

The reaction of 3-(1-propylpiperidin-3(S)-yl)phenol (I) with trifluoromethanesulfonic anhydride gives the triflate (II), which is treated with Pd(OAc)4, CO and MeOH, yielding 3-(1-propylpiperidin-3(S)-yl)benzoic acid methyl ester (III). The reaction of (III) with sodium azide and H2SO4 affords the aniline (IV), which by reaction with NaNO2, HBr and CuBr provides 3(S)-(3-bromophenyl)-1-propylpiperidine (V). The reaction of (V) with dimethyl disulfide and n-BuLi gives the thioether (VI), which is oxidized with MCPBA to afford the target sulfone, which is easily separated from the N-oxide (VII) also formed in the oxidation process. The N-oxide (VII) can be reduced to the target compound by means of TiCl4 and NaI in acetonitrile.

1 Sonesson, C.; et al.; Substituted (S)-phenylpiperidines and rigid congeners as preferential dopamine autoreceptor antagonists: Synthesis and structure-activity relationships. J Med Chem 1994, 37, 17, 2735.
2 Svensson, K.A.I.; Wikström, H.V.; Carlsson, P.A.E.; Boije, A.M.P.; Waters, R.N.; Sonesson, C.A.; Stjerulof, N.P.; Andersson, B.R. (Pharmacia Corp.); New centrally acting substd. phenylazacycloalkanes. EP 0641320; JP 1994509561; US 5462947; WO 9218475 .
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) 43383 methyl 3-[(3S)-1-propylpiperidinyl]benzoate C16H23NO2 详情 详情
(IV) 43384 3-[(3S)-1-propylpiperidinyl]phenylamine; 3-[(3S)-1-propylpiperidinyl]aniline C14H22N2 详情 详情
(V) 43385 (3S)-3-(3-bromophenyl)-1-propylpiperidine C14H20BrN 详情 详情
(VI) 43386 (3S)-3-[3-(methylsulfanyl)phenyl]-1-propylpiperidine; methyl 3-[(3S)-1-propylpiperidinyl]phenyl sulfide C15H23NS 详情 详情
(VII) 43387 (3S)-3-[3-(methylsulfonyl)phenyl]-1-propyl-1-piperidiniumolate C15H23NO3S 详情 详情
Extended Information