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【结 构 式】

【分子编号】48488

【品名】methyl (3aS,4R,11bR)-3-benzyl-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate

【CA登记号】

【 分 子 式 】C31H38N2O5

【 分 子 量 】518.6532

【元素组成】C 71.79% H 7.38% N 5.4% O 15.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIIIa)

In an alternative procedure, aldehyde (II) was condensed with the indoloazepine (VIII) bearing a chiral N-alpha-ferrocenylethyl substituent to provide an equimolecular mixture of two separable C-20 epimeric diastereomers (IX) and (X), each accompanied by a minor diastereoisomeric byproduct. Cleavage of the ferrocenyl substituent with HOAc at 70 C provided the secondary amines (XI) and (XII). In this cleavage, the C-3,C-7 epimeric products were formed in 12% yield and were separated by chromatography. The major secondary amines (XI) and (XII) were N-benzylated to provide the corresponding tertiary amines (XIII). Reductive ring cleavage, followed by hydrogenolysis of the N-benzyl group, then gave the tricyclic compounds (VI), which were cyclized and rearranged as above.

1 Kuehne, M.E.; et al.; Enantioselective syntheses of coronaridine and 18-methoxycoronaridine. Tetrahedron 2001, 57, 11, 2085.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIa) 48480 methyl (5R,7S)-5-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-carboxylate C24H34N2O5 详情 详情
(VIb) 48481 methyl (5R,7S)-5-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-carboxylate C24H34N2O5 详情 详情
(XIIIa) 48488 methyl (3aS,4R,11bR)-3-benzyl-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C31H38N2O5 详情 详情
(XIIIb) 48489 methyl (3aS,4R,11bR)-3-benzyl-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C31H38N2O5 详情 详情
(II) 48474 4-(1,3-dioxolan-2-yl)-6-methoxyhexanal C10H18O4 详情 详情
(VIII) 48483   C38H39FeN2O2P 详情 详情
(IX) 48484   C48H55FeN2O5P 详情 详情
(X) 48485   C48H55FeN2O5P 详情 详情
(XI) 48486 methyl (3aS,4R,11bR)-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C24H32N2O5 详情 详情
(XII) 48487 methyl (3aS,4R,11bR)-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C24H32N2O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XIIIa)

In an improved synthesis, condensation of the beta-dimethyltetramethylene-ferrocene derivative (XIV) with aldehyde (II) produced the unseparable C-20 epimeric mixture (XV) without appreciable amounts of diastereomeric byproducts. Cleavage of the chiral auxiliary group with HOAc under milder conditions furnished the secondary amines (XVI) with minimal C-3,C-7 epimerization. Benzylation of amines (XVI) then gave the enantiomerically pure tertiary amines (XIII), which were finally processed as above.

1 Kuehne, M.E.; et al.; Enantioselective syntheses of coronaridine and 18-methoxycoronaridine. Tetrahedron 2001, 57, 11, 2085.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVIa) 48486 methyl (3aS,4R,11bR)-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C24H32N2O5 详情 详情
(XVIb) 48487 methyl (3aS,4R,11bR)-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C24H32N2O5 详情 详情
(XIIIa) 48488 methyl (3aS,4R,11bR)-3-benzyl-4-[(2R)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C31H38N2O5 详情 详情
(XIIIb) 48489 methyl (3aS,4R,11bR)-3-benzyl-4-[(2S)-2-(1,3-dioxolan-2-yl)-4-methoxybutyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate C31H38N2O5 详情 详情
(XVa) 48491   C40H52FeN2O5 详情 详情
(XVb) 48492   C40H52FeN2O5 详情 详情
(II) 48474 4-(1,3-dioxolan-2-yl)-6-methoxyhexanal C10H18O4 详情 详情
(XIV) 48490   C30H36FeN2O2 详情 详情
Extended Information