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

HRID 585080ノート

反応式

HRID 585080 の反応式
[CH2:1]1[CH2:11][CH2:10]N2C(=NCCC2)[CH2:3][CH2:2]1.BrCCCCCBr.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]2[C:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[C:28]3[C:37]4[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=4)[CH2:31][CH2:30][N:29]3[C:42]=2[CH3:43])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[CH3:41][O:40][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][C:35]=1[O:38][CH3:39])[C:28]1=[C:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([N:19]4[CH2:10][CH2:11][CH2:1][CH2:2][CH2:3]4)[CH:21]=3)=[C:42]([CH3:43])[N:29]1[CH2:30][CH2:31]2

参加物

5

反応物 3

HCID 81001,5-DibromopentaneHCID 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 10227320Ethyl 8,9-dimethoxy-3-methyl-2-(3-piperidinyl-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 84.9 mg (0.37 mmol) of 1,5-dibromopentane 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 (Example 28) in 3 mL of DMF. The mixture was stirred at 120° C. for 20 hours, then 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. customevaporated under reduced pressure
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure
  7. customfollowed by crystallization from diethyl ether

出典と根拠

ORDレコード
ord-0246abcbbc7649d8aa3ea9145c71d2ce
出典データセット
uspto-grants-2005_08
特許番号
US06930114B2

反応ノート

読み込み中…