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【结 构 式】

【分子编号】30432

【品名】4-[(1-nitrocyclopentyl)methyl]phenol

【CA登记号】

【 分 子 式 】C12H15NO3

【 分 子 量 】221.25604

【元素组成】C 65.14% H 6.83% N 6.33% O 21.69%

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:(III)

The condensation of 4-hydroxybenzyl alcohol (I) with nitrocyclopentane (II) by means of TBAF at 130 C gives 4-(1-nitrocyclopentylmethyl)phenol (III), which is reduced to the corresponding amine (IV) with hydrogen over Raney-Ni in methanol. The protection of the NH2 group of (IV) with di-tert-butyl dicarbonate affords the carbamate (V), which is condensed with the phosphinic ester (VI) by means of NaH in DMF giving the substituted phosphinate (VII). The elimination of the carbamate group of (VII) with TFA in dichloromethane yields the cyclopenatylamine (VIII), which is condensed with the chiral oxirane (IX) in refluxing methanol affording the substituted aminopropanol (X). Elimination of the benzyl protecting group of (X) gives the intermediate phosphinic ester (XI) that is finally hydrolyzed with LiOH in methanol.

1 Beeley, L.J.; Berge, J.M.; Dean, D.K.; Rami, H.K. (SmithKline Beecham plc); Phosphorus containing aryloxy or arylthiopropanolamine derivs.. WO 9822480 .
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) 29474 4-(hydroxymethyl)phenol; 4-hydroxyphenylmethanol 4-hydroxybenzenemethanol; 4-Hydroxybenzyl alcohol 623-05-2 C7H8O2 详情 详情
(II) 30431 1-nitrocyclopentane 2562-38-1 C5H9NO2 详情 详情
(III) 30432 4-[(1-nitrocyclopentyl)methyl]phenol C12H15NO3 详情 详情
(IV) 30433 4-[(1-aminocyclopentyl)methyl]phenol C12H17NO 详情 详情
(V) 30434 tert-butyl 1-(4-hydroxybenzyl)cyclopentylcarbamate C17H25NO3 详情 详情
(VI) 30435 [ethoxy(phenyl)phosphoryl]methyl 4-chlorobenzenesulfonate C15H16ClO5PS 详情 详情
(VII) 30436 ethyl [4-([1-[(tert-butoxycarbonyl)amino]cyclopentyl]methyl)phenoxy]methyl(phenyl)phosphinate C26H36NO5P 详情 详情
(VIII) 30437 ethyl [4-[(1-aminocyclopentyl)methyl]phenoxy]methyl(phenyl)phosphinate C21H28NO3P 详情 详情
(IX) 30438 benzyl 4-[(2S)oxiranylmethoxy]phenyl ether; (2S)-2-[[4-(benzyloxy)phenoxy]methyl]oxirane C16H16O3 详情 详情
(X) 30439 ethyl (4-[[1-([(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino)cyclopentyl]methyl]phenoxy)methyl(phenyl)phosphinate C37H44NO6P 详情 详情
(XI) 30440 ethyl [4-[(1-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]cyclopentyl)methyl]phenoxy]methyl(phenyl)phosphinate C30H38NO6P 详情 详情
Extended Information