Sodium hydride → Ethyl 4-[N-cyclopropylmethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

HRID 1097381ノート

反応式

HRID 1097381 の反応式
[H-].[Na+].[CH:3]1[C:14]2=[C:15]3[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9][CH2:8][CH2:7][C:6]3=[CH:5][C:4]=1[NH:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1.Br[CH2:29][CH:30]1[CH2:32][CH2:31]1.[Cl-].[NH4+]>CN(C)C=O>[CH:30]1([CH2:29][N:16]([C:4]2[CH:3]=[C:14]3[C:15]4[CH:10]([CH2:11][CH2:12][CH2:13]3)[CH2:9][CH2:8][CH2:7][C:6]=4[CH:5]=2)[C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)[CH2:32][CH2:31]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 81503BromomethylcyclopropaneHCID 66811225Ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

生成物 1

HCID 58526561Ethyl 4-[N-cyclopropylmethyl-(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of sodium hydride (60%, 0.009 g) in N,N-dimethylformamide (2 ml) was added with ethyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.033 g) dissolved in N,N-dimethylformamide (1 ml), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was added with bromomethylcyclopropane (0.02 ml), the mixture was stirred at room temperature for 2 hours, and then added with saturated aqueous ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50) to obtain the title compound (0.037 g, yield: 97%).

後処理

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:50)

出典と根拠

ORDレコード
ord-d062824a2a064cb480dbecd7a3ce6775
出典データセット
uspto-grants-2012_03
特許番号
US08143260B2

反応ノート

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