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【结 构 式】

【分子编号】43283

【品名】tert-butyl (5S)-3-bromo-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate

【CA登记号】

【 分 子 式 】C23H34BrNO3

【 分 子 量 】452.4319

【元素组成】C 61.06% H 7.57% Br 17.66% N 3.1% O 10.61%

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:(XXI)

An alternative procedure has been reported for the synthesis of the chiral (S)-amine (XXIV). Ketone (IX) was treated with O-methyl hydroxylamine to afford a geometric mixture of O-methyl oximes, from which isomer (XVII) was isolated by silica gel chromatography. Asymmetric reduction of the O-methyl oxime (XVII) with borane in the presence of the chiral auxiliary (XVIII) furnished the desired (S)-amine (XIX), which was further protected as the tert-butyl carbamate (XX) by treatment with Boc2O. Bromide (XXI), carboxylic acid (XXII) and amide (XXIII) were obtained following the same procedures as above. Then, acid cleavage of the Boc group of (XXIII) yielded the chiral amine (XXIV).

1 Bohacek, R.; Yang, M.; Shakespeare, W.; et al.; Structure-based design of an osteoclast-selective, nonpeptide Src homology 2 inhibitor with in vivo antiresorptive activity. Proceedings of the National Academy of Sciences of the United States of America 2000, 97, 17, 9373.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 43271 2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one C18H24O2 详情 详情
(XVII) 43279 2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one O-methyloxime C19H27NO2 详情 详情
(XVIII) 10103 (2R)-2-Amino-3-methyl-1,1-diphenyl-1-butanol 56755-20-5 (hydrochloride) C17H21NO 详情 详情
(XIX) 43281 (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylamine; (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-amine C18H27NO 详情 详情
(XX) 43282 tert-butyl (5S)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate C23H35NO3 详情 详情
(XXI) 43283 tert-butyl (5S)-3-bromo-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate C23H34BrNO3 详情 详情
(XXII) 43284 (9S)-9-[(tert-butoxycarbonyl)amino]-3-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-2-carboxylic acid C24H35NO5 详情 详情
(XXIII) 43285 tert-butyl (5S)-3-(aminocarbonyl)-2-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-ylcarbamate C24H36N2O4 详情 详情
(XXIV) 43286 (9S)-9-amino-3-(cyclohexylmethoxy)-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene-2-carboxamide C19H28N2O2 详情 详情
Extended Information