(2S)-1-(benzylamino)-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol -Drug Synthesis Database

【结构式】

【分子编号】35073

【品名】(2S)-1-(benzylamino)-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol

【CA登记号】

【分子式】C₂₃H₃₃N₃O₂

【分子量】383.53404

【元素组成】C 72.03% H 8.67% N 10.96% O 8.34%

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：(IX)

(S)-Epichlorhydrin (V) was treated with benzylamine to afford aminoalcohol (VI). After protection of the amino group of (VI) as the tert-butyl carbamate (VII) with Boc2O, displacement of the chlorine of (VII) with arylpiperazine (I) furnished (VIII). Deprotection of the N-Boc group of (VIII) by means of trifluoroacetic acid gave (IX). Then, the N-benzyl group of (IX) was removed by transfer hydrogenolysis employing ammonium formate and Pd/C to provide the intermediate amine (IV).

参考文献中间体

合成目标

【1】 Prouty, C.; Wang, J.; Kuo, G.-H.; Pulito, V.; Murray, W.V.; Cheung, P.; Jolliffe, L.; Varga, S.; Evangelisto, M.; Design, synthesis, and structure-activity relationships of phthalimide-phenylpiperazines: A novel series of potent and selective alpha1a-adrenergic receptor antagonists. J Med Chem 2000, 43, 11, 2183.
【2】 Murray, W.V.; Kuo, G.-H.; Prouty, C.P. (Ortho-McNeil Pharmaceutical, Inc.); Phthalimido arylpiperazines as alpha 1a receptor antagonists useful in the treatment of benign prostatic hyperplasia. US 6063785; WO 9942445 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(I)	35066	isopropyl 2-(1-piperazinyl)phenyl ether; 1-(2-isopropoxyphenyl)piperazine		C₁₃H₂₀N₂O	详情	详情
(IV)	35069	(2S)-1-amino-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol		C₁₆H₂₇N₃O₂	详情	详情
(V)	13917	(S)-Epichlorohydrin; (2S)-2-(Chloromethyl)oxirane;(S)-(+)-epichlorohydrin	67843-74-7	C₃H₅ClO	详情	详情
(VI)	35070	(2S)-1-(benzylamino)-3-chloro-2-propanol		C₁₀H₁₄ClNO	详情	详情
(VII)	35071	tert-butyl benzyl[(2S)-3-chloro-2-hydroxypropyl]carbamate		C₁₅H₂₂ClNO₃	详情	详情
(VIII)	35072	tert-butyl benzyl[(2R)-2-hydroxy-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]propyl]carbamate		C₂₈H₄₁N₃O₄	详情	详情
(IX)	35073	(2S)-1-(benzylamino)-3-[4-(2-isopropoxyphenyl)-1-piperazinyl]-2-propanol		C₂₃H₃₃N₃O₂	详情	详情

Extended Information