(2R)-2-{[(E)-1,3-benzodioxol-5-ylmethylidene]amino}-2-phenyl-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】53637

【品名】(2R)-2-{[(E)-1,3-benzodioxol-5-ylmethylidene]amino}-2-phenyl-1-ethanol

【CA登记号】n/a

【分子式】C₁₆H₁₅NO₃

【分子量】269.30004

【元素组成】C 71.36% H 5.61% N 5.2% O 17.82%

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：(XXV)

Preparation of the intermediate chiral amine (XVII) was reported by a number of synthetic strategies. Piperonal (X) was condensed with D-phenylglycinol (XXIV) to give imine (XXV). Diastereoselective addition of allylmagnesium chloride (XXVI) to imine (XXV) afforded amine (XXVII). Simultaneous hydrogenation of the double bond and hydrogenolysis of the chiral auxiliary of (XXVII) furnished the desired amine (XVII).

参考文献中间体

合成目标

【1】 Storace, L.; et al.; An efficient large-scale process for the human leukocyte elastase inhibitor, DMP 777. Org Process Res Dev 2002, 6, 1, 54.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(XVII)	53631	(1R)-1-(1,3-benzodioxol-5-yl)-1-butanamine; (1R)-1-(1,3-benzodioxol-5-yl)butylamine	n/a	C₁₁H₁₅NO₂	详情	详情
(XXIV)	14376	(2R)-2-amino-2-phenyl-1-ethanol; (R)-(-)-2-phenylglycinol; (R)-2-amino-2-phenyl-1-ethanol	56613-80-0	C₈H₁₁NO	详情	详情
(XXV)	53637	(2R)-2-{[(E)-1,3-benzodioxol-5-ylmethylidene]amino}-2-phenyl-1-ethanol	n/a	C₁₆H₁₅NO₃	详情	详情
(XXVI)	53638	allyl(chloro)magnesium	2622-05-1	C₃H₅ClMg	详情	详情
(XXVII)	53639	(2R)-2-{[(1R)-1-(1,3-benzodioxol-5-yl)-3-butenyl]amino}-2-phenyl-1-ethanol	n/a	C₁₉H₂₁NO₃	详情	详情

Extended Information