2-[(3S)-5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile -Drug Synthesis Database

【结构式】

【分子编号】58089

【品名】2-[(3S)-5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile

【CA登记号】

【分子式】C₁₃H₁₄N₂O₂

【分子量】230.26644

【元素组成】C 67.81% H 6.13% N 12.17% O 13.9%

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：(XII)

Condensation of 5-methoxy-1,3-dimethyl-2,3-dihydro-1H-indol-2-one (IV) with 2-chloroacetonitrile (XI) by means of a chiral phase transfer catalyst gives 2-(5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-y)-acetonitrile, which is separated into enantiomers by chromatography. Reductocyclization of the (S)-enantiomer (XII) by means of Vitride affords (3aS)-N1-noresermethole (XIII), which is submitted to a reductive methylation to provide esermethole (X). O-demethylation of (X) by means of BBr3 or AlCl3 gives eseroline (II), which is finally condensed with phenyl isocyanate.

参考文献中间体

合成目标

【1】 Castañer, J.; Sorbera, L.A.; Phenserine Tartrate. Drugs Fut 2003, 28, 1, 18.
【2】 Greig, N.H.; Pei, X.-F.; Brossi, A.; Phenserine, a novel anticholinesterase related to physostigmine: Total synthesis and biological properties. Aust J Chem 1996, 49, 2, 171.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	20365	(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol		C₁₃H₁₈N₂O	详情	详情
(III)	11289	1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate	103-71-9	C₇H₅NO	详情	详情
(IV)	58084	5-methoxy-1,3-dimethyl-1,3-dihydro-2H-indol-2-one		C₁₁H₁₃NO₂	详情	详情
(X)	58088	(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methyl ether; (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole		C₁₄H₂₀N₂O	详情	详情
(XI)	14443	2-chloroacetonitrile; chloroacetonitrile	107-14-2	C₂H₂ClN	详情	详情
(XII)	58089	2-[(3S)-5-methoxy-1,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-3-yl]acetonitrile		C₁₃H₁₄N₂O₂	详情	详情
(XIII)	58090	(3aS,8aR)-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methyl ether; (3aS,8aR)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole		C₁₃H₁₈N₂O	详情	详情

Extended Information