2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】30459

【品名】2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]-1-ethanol

【CA登记号】

【分子式】C₂₅H₂₉NO₂

【分子量】375.5108

【元素组成】C 79.96% H 7.78% N 3.73% O 8.52%

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：(XII)

The intermediate 2-(2(S)-amino-3-phenylpropoxy)ethanol (VII) has been obtained as follows: The condensation of 2(S)-(dibenzylamino)-3-phenyl-1-propanol (IX) with tert-butyl 2-bromoacetate (X) by means of tetrabutylammonium hydrogen sulfate and NaOH in dichloromethane/water gives 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]acetic acid tert-butyl ester (XI), which is reduced with LiAlH4 in THF yielding 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]ethanol (XII). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in methanol/acetic acid affording the target intermediate (VII).

参考文献中间体

合成目标

【1】 Brundish, D.E.; Brown, L.N.; Le Grand, D.M.; Menear, K.A.; Smith, G.P.; Allen, M.C.; Butler, P.I.; Cockroft, X.-L.; Matthews, I.T.W.; Walker, C.V.; Wathey, W.B. (Novartis AG); Thrombin inhibitors. WO 9746553 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	30455	2-[[(2S)-2-amino-3-phenylpropyl]oxy]-1-ethanol		C₁₁H₁₇NO₂	详情	详情
(IX)	30457	(2S)-2-(dibenzylamino)-3-phenyl-1-propanol	111060-52-7	C₂₃H₂₅NO	详情	详情
(X)	17430	2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate	5292-43-3	C₆H₁₁BrO₂	详情	详情
(XI)	30458	tert-butyl 2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]acetate		C₂₉H₃₅NO₃	详情	详情
(XII)	30459	2-[[(2S)-2-(dibenzylamino)-3-phenylpropyl]oxy]-1-ethanol		C₂₅H₂₉NO₂	详情	详情

Extended Information