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【结 构 式】

【分子编号】49551

【品名】3-(4-fluorophenoxy)-1-(3,4,4-trimethoxy-1-piperidinyl)-1-propanone

【CA登记号】

【 分 子 式 】C17H24FNO5

【 分 子 量 】341.3797032

【元素组成】C 59.81% H 7.09% F 5.57% N 4.1% O 23.43%

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 condensation of 3-(4-fluorophenoxy)propionic acid (I) with 4-piperidone (II) by means of pivaloyl chloride and TEA in refluxing toluene gives the amide (III), which is submitted to oxidation with diacetoxyiodobenzene and KOH in methanol, yielding the hydroxy-dimethoxyketal (IV). The methylation of the OH group of (IV) with Me-I and Ag2O in DMF affords the corresponding methoxy compound (V), which is hydrolyzed with HOAc to provide the methoxypiperidone (VI). The reaction of (VI) with O-benzylhydroxylamine (VII) and pyridine in refluxing toluene gives the oxime (VIII), which is diastereoselectively reduced with BH3 in THF, yielding the cis-isomer (IX). Finally, this amine is condensed with 4-amino-5-chloro-2-methoxybenzoic acid (X) by means of ethyl chloroformate, TEA and HOBt in DMF to afford the target amide.

1 Cossy, J.; et al.; A short synthesis of cisapride: A gastrointestinal stimulant derived from cis-4-amino-3-methoxypiperidine. Tetrahedron Lett 2001, 42, 33, 5713.
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) 39121 3-(4-fluorophenoxy)propionic acid 2967-70-6 C9H9FO3 详情 详情
(II) 27115 4-piperidinone 40064-34-4 C5H9NO 详情 详情
(III) 49549 1-[3-(4-fluorophenoxy)propanoyl]-4-piperidinone C14H16FNO3 详情 详情
(IV) 49550 3-(4-fluorophenoxy)-1-(3-hydroxy-4,4-dimethoxy-1-piperidinyl)-1-propanone C16H22FNO5 详情 详情
(V) 49551 3-(4-fluorophenoxy)-1-(3,4,4-trimethoxy-1-piperidinyl)-1-propanone C17H24FNO5 详情 详情
(VI) 49552   C15H18FNO4 详情 详情
(VII) 14640 O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene 622-33-3 C7H9NO 详情 详情
(VIII) 49553 1-[3-(4-fluorophenoxy)propanoyl]-3-methoxy-4-piperidinone O-benzyloxime C22H25FN2O4 详情 详情
(IX) 49554 (3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinamine; (3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidinylamine C15H23FN2O2 详情 详情
(X) 12419 4-Amino-5-chloro-2-methoxybenzoic acid 7206-70-4 C8H8ClNO3 详情 详情
Extended Information