allyl(chloro)magnesium -Drug Synthesis Database

【结构式】

【分子编号】53638

【品名】allyl(chloro)magnesium

【CA登记号】2622-05-1

【分子式】C₃H₅ClMg

【分子量】100.8304

【元素组成】C 35.74% H 5% Cl 35.16% Mg 24.1%

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：(XXVI)

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

合成路线2

该中间体在本合成路线中的序号：(LX)

In a different procedure, addition of the allyl Grignard reagent (LX) to the N-methoxy amide (LIX), provided ketone (LXI). Subsequent addition of methylmagnesium chloride to (LXI) led to the tertiary alcohol (LXII), which was converted to the methyl ether (LXIII) by alkylation with iodomethane and NaH. Acetonide (LXIII) hydrolysis with p-toluenesulfonic acid in MeOH gave the N-Boc amino alcohol (LXIV). The olefin double bond of (LXIV) was then hydrogenated over Pd/C to the propyl derivative (LXV). Oxidation of alcohol (LXV) under modified Swern conditions furnished aldehyde (LXVI). This was then condensed with p-methoxybenzyl hydroxylamine (LXVII), leading to the nitrone (LXVIII).

参考文献中间体

合成目标

【1】 Hanessian, S.; et al.; Total synthesis of A-315675: A potent inhibitor of influenza neuraminidase. J Am Chem Soc 2002, 124, 17, 4716.
【2】 Inhibitors of neuraminidases. WO 0128996 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(LIX)	55202	tert-butyl (4R)-4-{[methoxy(methyl)amino]carbonyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₁₃H₂₄N₂O₅	详情	详情
(LX)	53638	allyl(chloro)magnesium	2622-05-1	C₃H₅ClMg	详情	详情
(LXI)	55203	tert-butyl (4R)-4-(3-butenoyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₁₄H₂₃NO₄	详情	详情
(LXII)	55204	tert-butyl (4R)-4-[(1S)-1-hydroxy-1-methyl-3-butenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₁₅H₂₇NO₄	详情	详情
(LXIII)	55205	tert-butyl (4R)-4-[(1S)-1-methoxy-1-methyl-3-butenyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate		C₁₆H₂₉NO₄	详情	详情
(LXIV)	55206	tert-butyl (1R,2S)-1-(hydroxymethyl)-2-methoxy-2-methyl-4-pentenylcarbamate		C₁₃H₂₅NO₄	详情	详情
(LXV)	55207	tert-butyl (1R,2S)-1-(hydroxymethyl)-2-methoxy-2-methylpentylcarbamate		C₁₃H₂₇NO₄	详情	详情
(LXVI)	55208	tert-butyl (1S,2S)-1-formyl-2-methoxy-2-methylpentylcarbamate		C₁₃H₂₅NO₄	详情	详情
(LXVII)	55209	1-[(hydroxyamino)methyl]-4-methoxybenzene; N-(4-methoxybenzyl)hydroxylamine		C₈H₁₁NO₂	详情	详情
(LXVIII)	55210	{(Z,2R,3S)-2-[(tert-butoxycarbonyl)amino]-3-methoxy-3-methylhexylidene}(4-methoxybenzyl)ammoniumolate		C₂₁H₃₄N₂O₅	详情	详情

Extended Information