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【结 构 式】

【分子编号】53259

【品名】(1R,2S,3S,5R)-2-bromo-3-{[tert-butyl(dimethyl)silyl]oxy}bicyclo[3.2.0]heptan-6-one

【CA登记号】n/a

【 分 子 式 】C13H23BrO2Si

【 分 子 量 】319.31392

【元素组成】C 48.9% H 7.26% Br 25.02% O 10.02% Si 8.8%

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)

Synthesis of the tricyclic ketone intermediate (VI): Optical resolution of racemic bicyclo[3.2.0]hept-2-en-6-one (I) by reaction with SO2 and (+)-a-methylbenzylamine (II) yields a mixture of diastereomeric salts of the a-hydroxysulfonic acid with the chiral amine (II), which are separated by crystallization. Treatment of the purified salt (III) with aqueous Na2CO3 results in the pure enantiomer (­)-(I). Reaction of (­)-(I) with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in acetone/water affords the bromohydrin (IV), which is treated with TBDMS-Cl and imidazole to provide the silyl ether (V). Finally, reaction of the protected bromohydrin (V) with potassium tert-butoxide in toluene gives the target tricyclic ketone intermediate (VI).

1 Boulton, L.T.; Brick, D.; Fox, M.E.; et al.; Synthesis of the potent antiglaucoma agent, travoprost. Org Process Res Dev 2002, 6, 2, 138.
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) 24421 (1S,5R)bicyclo[3.2.0]hept-2-en-6-one C7H8O 详情 详情
(rac)-(I) 53261 bicyclo[3.2.0]hept-2-en-6-one 13173-09-6 C7H8O 详情 详情
(II) 10039 (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine 3886-69-9 C8H11N 详情 详情
(III) 53267 Butanoic acid; Butyric acid; N-Butanic acid; N-Butanoic acid; n-Butyric acid; N-Ethylacetic acid; N-Propanecarboxylic acid; N-Propylformic acid 107-92-6 C4H8O2 详情 详情
(IV) 53258 (1R,2S,3S,5R)-2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one n/a C7H9BrO2 详情 详情
(V) 53259 (1R,2S,3S,5R)-2-bromo-3-{[tert-butyl(dimethyl)silyl]oxy}bicyclo[3.2.0]heptan-6-one n/a C13H23BrO2Si 详情 详情
(VI) 53260 (1R,3S,5R)-3-{[tert-butyl(dimethyl)silyl]oxy}tricyclo[3.2.0.0~2,7~]heptan-6-one n/a C13H22O2Si 详情 详情
Extended Information