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【结 构 式】

【分子编号】61348

【品名】methyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-cyanopentanoate

【CA登记号】

【 分 子 式 】C18H20N2O5

【 分 子 量 】344.36728

【元素组成】C 62.78% H 5.85% N 8.13% O 23.23%

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:(XVIII)

3-(Carbomethoxy)propionyl chloride (XV) is condensed with the chiral oxazolidine (XVI) to provide (XVII). Titanium-catalyzed Michael addition of acrylonitrile to the N-acyl oxazolidine (XVII) affords nitrile (XVIII), which is reduced to the primary amine (XIX) by catalytic hydrogenation in the presence of PtO2. Reductive alkylation of amine (XIX) with N-Boc-4-piperidone (XX) gives rise to the aminopiperidine (XXI). This is then cyclized to the piperidinyl piperidone (XXII) upon heating in acetonitrile. After alkaline hydrolysis of the methyl ester group of (XXII), coupling of the resultant acid (XXIII) with methylamine gives rise to the corresponding amide (XXIV). The N-Boc protecting group of (XXIV) is then removed by treatment with trifluoroacetic acid to furnish piperidine (XXV)

1 Carruthers, N.I.; Alaimo, C.A.; Shih, N.-Y.; Lavey, B.J.; Ting, P.C.; Reichard, G.A. (Schering Corp.); Substd. oximes as neurokinin antagonists. EP 1032561; WO 9926924 .
2 Carruthers, N.I.; Reichard, G.A.; Shih, N.-Y.; Lavey, B.J.; Alaimo, C.A.; Ting, P.C. (Schering Corp.); Substd. oximes as neurokinin antagonists. US 6063926 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(XV) 18060 4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate 1490-25-1 C5H7ClO3 详情 详情
(XVI) 25351 (4R)-4-benzyl-1,3-oxazolidin-2-one; (R)-(+)-4-benzyl-2-oxazolidinone 102029-44-7 C10H11NO2 详情 详情
(XVII) 61347 methyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate C15H17NO5 详情 详情
(XVIII) 61348 methyl (3R)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-5-cyanopentanoate C18H20N2O5 详情 详情
(XIX) 61349 methyl (3R)-6-amino-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}hexanoate C18H24N2O5 详情 详情
(XX) 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
(XXI) 61350 tert-butyl 4-[((4R)-4-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-6-methoxy-6-oxohexyl)amino]-1-piperidinecarboxylate C28H41N3O7 详情 详情
(XXII) 61351   C18H30N2O5 详情 详情
(XXIII) 61352   C17H28N2O5 详情 详情
(XXIV) 61353   C18H31N3O4 详情 详情
(XXV) 61354   C13H23N3O2 详情 详情
Extended Information