Ethyl bromoacetate → N-benzyl-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine

HRID 274045ノート

反応式

HRID 274045 の反応式
[CH2:1]([NH:8][CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[Cl-].[NH4+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([NH:8][CH:9]1[CH2:10][CH2:11][CH2:12][C:13]2[CH:19]=[CH:18][C:17]([O:20][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:16][C:14]=2[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18007284HCID 18007284、化合物

生成物 1

HCID 18007287N-benzyl-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒2 回

反応条件

温度
70 °C

実験手順

To an ice-cooled solution of 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (1.7 g) in toluene (56 ml) was added portionwise sodium hydride (60% dispersion in mineral oil; 0.31 g). After the addition was complete, the mixture was stirred at 70° C. for 1 hour. After cooling, a mixture of ethyl bromoacetate (0.81 ml) and tetra-n-butylammonium bromide (0.10 g) in toluene (14 ml) was added, and the mixture was stirred at 70° C. for 4 hours. After cooling, the reaction mixture was poured into saturated aqueous ammonium chloride, and extracted once with ethyl acetate. The extract was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform-ethanol; 25:1 to 5:1) to give N-benzyl-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (2.0 g) as an oil.

後処理

  1. additionAfter the addition
  2. temperatureAfter cooling
  3. additionwas added
  4. stirringthe mixture was stirred at 70° C. for 4 hours
  5. temperatureAfter cooling
  6. extractionextracted once with ethyl acetate
  7. washThe extract was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (gradient elution; chloroform-ethanol; 25:1 to 5:1)

出典と根拠

ORDレコード
ord-917169f2c68442e1b65b96da33f0367f
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

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