1,4-Dibromobutane → Ethyl 8,9dimethoxy-3-methyl-2-(3-pyrrolidinyl-phenyl)-5,6-dihydro-pyrrolo[2,1-a]-isoquinoline-1-carboxylate

HRID 585083ノート

反応式

HRID 585083 の反応式
[CH2:1]1[CH2:11]CN2C(=NCCC2)[CH2:3][CH2:2]1.BrCCCCBr.[NH2:18][C:19]1[CH:20]=[C:21]([C:25]2[C:26]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:27]3[C:36]4[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=4)[CH2:30][CH2:29][N:28]3[C:41]=2[CH3:42])[CH:22]=[CH:23][CH:24]=1>CN(C=O)C>[CH3:40][O:39][C:33]1[CH:32]=[C:31]2[C:36](=[CH:35][C:34]=1[O:37][CH3:38])[C:27]1=[C:26]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([N:18]4[CH2:3][CH2:2][CH2:1][CH2:11]4)[CH:20]=3)=[C:41]([CH3:42])[N:28]1[CH2:29][CH2:30]2

参加物

5

反応物 3

HCID 80561,4-DibromobutaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10179495Ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate

生成物 1

HCID 20823072Ethyl 8,9dimethoxy-3-methyl-2-(3-pyrrolidinyl-phenyl)-5,6-dihydro-pyrrolo[2,1-a]-isoquinoline-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

168.5 mg (1.11 mmol) of DBU and 79.9 mg (0.37 mmol) of 1,4-dibromobutane were added to a solution of 150 mg (0.37 mmol) of ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate obtained as described above in 3 mL of DMF. The mixture was stirred at 120° C. for 20 hours, the solvent was evaporated under reduced pressure, and the residue was taken up in an ethyl acetate/water mixture. The layers were separated, the aqueous layer was extracted with ethyl acetate, and the combined organic phases were washed with water, dried over Na2SO4 and the solvent was evaporated under reduced pressure. Chromatography on a short silica gel column using a dichloromethane/ethyl acetate 10:1 mixture as eluant, followed by crystallization from diethyl ether gave the title compound.

後処理

  1. customobtained
  2. customthe solvent was evaporated under reduced pressure
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated under reduced pressure
  8. customfollowed by crystallization from diethyl ether

出典と根拠

ORDレコード
ord-3a76fa43c38a485fb40acf71316014d6
出典データセット
uspto-grants-2005_08
特許番号
US06930114B2

反応ノート

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