methyl 3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】60857

【品名】methyl 3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxybenzoate

【CA登记号】

【分子式】C₂₃H₃₁NO₃

【分子量】369.50408

【元素组成】C 74.76% H 8.46% N 3.79% O 12.99%

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：(IV)

The known aminoacid (I) is esterified to (II) employing methanolic H2SO4. Ester group reduction in (II) with LiAlH4 yields alcohol (III). The O-benzyl group of (III) is then removed by catalytic hydrogenation in the presence of Raney nickel, providing phenol (V). Alternatively, compound (III) is converted into diol (V) by O-benzyl group hydrogenolysis, followed by LiAlH4 reduction of the resultant ester (IV). Finally, selective monoesterification of diol (V) with isobutyryl chloride (VI) and triethylamine gives rise to the title compound.

参考文献中间体

合成目标

【1】 Sorbera, L.A.; Castaner, J.; Leeson, P.A.; Fesoterodine. Drugs Fut 2003, 28, 7, 647.
【2】 Meese, C. (Schwarz Pharma AG); Stable salts of novel derivs. of 3,3-diphenylpropylamines. DE 19955190; JP 2003514018; WO 0135957 .

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)	60854	4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]benzoic acid		C₂₉H₃₅NO₃	详情	详情
(II)	60855	methyl 4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]benzoate		C₃₀H₃₇NO₃	详情	详情
(III)	60856	{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}methanol		C₂₉H₃₇NO₂	详情	详情
(IV)	60857	methyl 3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxybenzoate		C₂₃H₃₁NO₃	详情	详情
(V)	60858	2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol		C₂₂H₃₁NO₂	详情	详情
(VI)	14932	isobutyryl chloride; 2-methylpropanoyl chloride	79-30-1	C₄H₇ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Ahman JB, Dillon BR, Pettman AJ. 2007. Process for the production of benzopyran-2-ol derivatives. WO 2007138440.
【2】 Browne R, Killkell M. 2007. New synthesis of substituted hydroxymethyl phenols. WO 2007137799.
【3】 Ennis S, Drews R, Meese C. 2007. Synthesis of phenolic esters of hydroxymethyl phenols. WO 2007140986.
【4】 Ennis S, Funchs C, Kanzler R, et al. 2007. Shortened synthesis using paraformaldehyde or trioxane. WO 2007114091.

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)	28205	4-hydroxybenzoic acid	99-96-7	C₇H₆O₃	详情	详情
(II)	10251	methyl 4-hydroxybenzoate; Methyl p-hydroxybenzoate	99-76-3	C₈H₈O₃	详情	详情
(III)	67146	2-oxo-4-phenylchroman-6-carboxylic acid		C₁₆H₁₂O₄	详情	详情
(IV)	67147	methyl 2-oxo-4-phenylchroman-6-carboxylate		C₁₇H₁₄O₄	详情	详情
(V)	60857	methyl 3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxybenzoate		C₂₃H₃₁NO₃	详情	详情

Extended Information