methyl 2-(benzyloxy)-5-[(2R)oxiranyl]benzoate -Drug Synthesis Database

【结构式】

【分子编号】62585

【品名】methyl 2-(benzyloxy)-5-[(2R)oxiranyl]benzoate

【CA登记号】

【分子式】C₁₇H₁₆O₄

【分子量】284.31164

【元素组成】C 71.82% H 5.67% O 22.51%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The intermediate chiral epoxide (V) has been obtained as follows: The bromination of 5-acetyl-2-benzyloxybenzoic acid methyl ester (I) with Br2 in chloroform gives the bromoacetyl derivative (II), which is submitted to a enantioselective reduction by means of BH3/THF catalyzed by the chiral oxazaborolidine (III) to yield the (R)-enantiomer (IV). Finally, this compound is cyclized by means of NaH in THF to afford the target (R)-epoxide (

参考文献中间体

合成目标

【1】 Hett, R.; et al.; Enantioselective synthesis of salmeterol via asymmetric borane reduction. Tetrahedron Lett 1994, 35, 50, 9375.

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)	62583	methyl 5-acetyl-2-(benzyloxy)benzoate		C₁₇H₁₆O₄	详情	详情
(II)	52356	methyl 5-(2-bromoacetyl)-2-[(phenylmethyl)oxy]benzoate		C₁₇H₁₅BrO₄	详情	详情
(III)	20631	(R)-Methyl oxazaborolidine; (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole	112022-83-0	C₁₈H₂₀BNO	详情	详情
(IV)	62584	methyl 2-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]benzoate		C₁₇H₁₇BrO₄	详情	详情
(V)	62585	methyl 2-(benzyloxy)-5-[(2R)oxiranyl]benzoate		C₁₇H₁₆O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The reaction of 6-(4-phenylbutoxy)hexyl bromide (VI) with NaN3 in DMF gives The azido derivative (VII), which is reduced with LiAlH4 to yield the primary amine (VIII). The reductive alkylation of (VIII) by means of benzaldehyde and NaBH4 affords the benzylamine (IX), which is condensed with the chiral epoxide (V) in refluxing THF to provide the chiral hydroxyamine (X). The reduction of the ester group of (X) with LiAlH4 leads to the hydroxymethyl compound (XI), which is finally fully debenzylated by means of H2 over Pd/C to give rise to the target (R)-salmeterol.

参考文献中间体

合成目标

【1】 Hett, R.; et al.; Enantioselective synthesis of salmeterol via asymmetric borane reduction. Tetrahedron Lett 1994, 35, 50, 9375.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	62585	methyl 2-(benzyloxy)-5-[(2R)oxiranyl]benzoate		C₁₇H₁₆O₄	详情	详情
(VI)	31479	1-[4-[(6-bromohexyl)oxy]butyl]benzene; 6-bromohexyl-4-phenylbutyl ether; 6-Bromohexyloxybutylbenzene	94749-73-2	C₁₆H₂₅BrO	详情	详情
(VII)	62586	1-{4-[(6-azidohexyl)oxy]butyl}benzene; 6-azidohexyl 4-phenylbutyl ether		C₁₆H₂₅N₃O	详情	详情
(VIII)	62577	6-(4-phenylbutoxy)-1-hexanamine; 6-(4-phenylbutoxy)hexylamine		C₁₆H₂₇NO	详情	详情
(IX)	35837	N-benzyl-6-(4-phenylbutoxy)-1-hexanamine; N-benzyl-N-[6-(4-phenylbutoxy)hexyl]amine		C₂₃H₃₃NO	详情	详情
(X)	62587	methyl 2-(benzyloxy)-5-((1R)-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)benzoate		C₄₀H₄₉NO₅	详情	详情
(XI)	62588	(1R)-1-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-ethanol		C₃₉H₄₉NO₄	详情	详情

Extended Information