【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% |
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 |