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【结 构 式】

【分子编号】63503

【品名】1,1-dimethylethyl 15-oxo-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-11-carboxylate

【CA登记号】

【 分 子 式 】C17H27NO5

【 分 子 量 】325.40512

【元素组成】C 62.75% H 8.36% N 4.3% O 24.58%

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:(VIII)

Alkylation of the spiro lactone (VI) with dibromide (VII) in the presence of lithium hexamethyldisilazide gives rise to the tricyclic spiro compound (VIII). After acidic Boc group cleavage in (VIII), the resultant secondary amine (IX) is reductively alkylated with aldehyde (V) to produce (X) as a diastereomeric mixture. Partial reduction of lactone (X) with DIBAL provides lactol (XI), which is further converted to nitrile (XII) upon treatment with cyanotrimethylsilane and boron trifluoride. Acidic hydrolysis of nitrile (XII), followed by esterification of the resultant carboxylic acid (XIII) furnishes the methyl ester (XIV)

1 Pyrrolidine antagonists of the CCR3 chemokine receptor. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 250.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(V) 63500 1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinecarbaldehyde C16H17NOS 详情 详情
(VI) 63501 1,1-dimethylethyl 2-oxo-1-oxa-8-azaspiro[4.5]decane-8-carboxylate C13H21NO4 详情 详情
(VII) 63502 1-bromo-2-[(2-bromoethyl)oxy]ethane; bis(2-bromoethyl) ether 5414-19-7 C4H8Br2O 详情 详情
(VIII) 63503 1,1-dimethylethyl 15-oxo-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-11-carboxylate C17H27NO5 详情 详情
(IX) 63504 3,14-dioxa-11-azadispiro[5.1.5.2]pentadecan-15-one C12H19NO3 详情 详情
(X) 63505 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecan-15-one C28H36N2O3S 详情 详情
(XI) 63506 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecan-15-ol C28H38N2O3S 详情 详情
(XII) 63507 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carbonitrile C29H37N3O2S 详情 详情
(XIII) 63508 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylic acid C29H38N2O4S 详情 详情
(XIV) 63509 methyl 11-{[1-(phenylmethyl)-4-(3-thiophenyl)-3-pyrrolidinyl]methyl}-3,14-dioxa-11-azadispiro[5.1.5.2]pentadecane-15-carboxylate C30H40N2O4S 详情 详情
Extended Information