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

HRID 274045노트

반응식

HRID 274045 반응식
[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

참가 물질

7

반응물 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18007284HCID 18007284, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매2회

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-917169f2c68442e1b65b96da33f0367f
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387710

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