tert-butyl (3S)-3-hydroxy-3-phenylpropylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】34900

【品名】tert-butyl (3S)-3-hydroxy-3-phenylpropylcarbamate

【CA登记号】

【分子式】C₁₄H₂₁NO₃

【分子量】251.32568

【元素组成】C 66.91% H 8.42% N 5.57% O 19.1%

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：(IV)

The enantioselective reduction of 2-benzoylacetonitrile (I) with BH3/Me2S complex catalyzed by the chiral catalyst (II) in THF gives 3(S)-hydroxy-3-phenylpropylamine (III), which is protected with tert-butyl dicarbonate and NaOH to yield the carbamate (IV). The condensation of (IV) with 4-(trifluoromethyl)phenol (V) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF affords N-[3(S)-phenyl-3-[4-(trifluoromethyl) phenoxy]propyl]carbamic acid tert-butyl ester (VI), which is finally reduced with LiAlH4 in refluxing THF to give the target (S)-Fluoxetine.

参考文献中间体

合成目标

【1】 Jurgens, A.R.; Hilborn, J.W. (Sepracor Inc.); Fluoxetine process from benzoylacetonitrile. WO 0007976 .

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)	34897	3-oxo-3-phenylpropanenitrile	614-16-4	C₉H₇NO	详情	详情
(II)	34898	(3aR,8aS)-2-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3,2]oxazaborole		C₁₀H₁₂BNO	详情	详情
(III)	34899	(1S)-3-amino-1-phenyl-1-propanol		C₉H₁₃NO	详情	详情
(IV)	34900	tert-butyl (3S)-3-hydroxy-3-phenylpropylcarbamate		C₁₄H₂₁NO₃	详情	详情
(V)	33607	4-(trifluoromethyl)phenol	402-45-9	C₇H₅F₃O	详情	详情
(VI)	34901	tert-butyl (3S)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylcarbamate		C₂₁H₂₄F₃NO₃	详情	详情

Extended Information