Chloroacetyl chloride → 1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone

HRID 1688030노트

반응식

HRID 1688030 반응식
Cl[CH2:2][C:3](Cl)=[O:4].[N+:6]([C:9]1[CH:19]=[CH:18][C:12]2[NH:13][CH2:14][CH2:15][CH2:16][O:17][C:11]=2[CH:10]=1)([O-:8])=[O:7].[CH2:20]([N:22](CC)[CH2:23][CH3:24])[CH3:21].N1CCCC1>CN(C)C1C=CN=CC=1.C(#N)C.C(Cl)Cl.O>[N+:6]([C:9]1[CH:19]=[CH:18][C:12]2[N:13]([C:3](=[O:4])[CH2:2][N:22]3[CH2:23][CH2:24][CH2:21][CH2:20]3)[CH2:14][CH2:15][CH2:16][O:17][C:11]=2[CH:10]=1)([O-:8])=[O:7]

참가 물질

9

반응물 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 31268PyrrolidineHCID 672641803-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

생성물 1

HCID 672641431-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone수율 74%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Chloroacetyl chloride (0.50 mL, 6.3 mmol; Acros) was added to a solution of 3-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.580 g, 2.99 mmol), Triethylamine (1.0 mL, 7.2 mmol), and 4-Dimethylaminopyridine (20 mg, 0.1 mmol; Acros) in Acetonitrile (40 mL) The reaction was stirred under an atmosphere of Nitrogen. After 3.5 h, Pyrrolidine (2.0 mL, 24 mmol) was added and stirred overnight. The mixture was diluted with DCM (30 mL) and water (30 mL), the layers separated and the aq. extracted with 10 mL DCM. The combined organics were washed with brine (20 mL) and dried, then conc. onto 4.5 g Celite. The residue was chromatographed (ISCO, 80 g Basic Alumina, 0-70% EtOAc:Hex) to afford 1-(3-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone as a yellow oil (664 mg, 74%). 1H-NMR (CDCl3): 7.92 (m, 2H), 7.44 (d, 1H, J=8.4 Hz), 4.2-4.6 (m, 4H), 3.15 (m, 2H), 2.48 (m, 4H), 2.10 (m, 2H), 1.70 (m, 4H).

후처리

  1. stirringstirred overnight
  2. customthe layers separated
  3. extractionthe aq. extracted with 10 mL DCM
  4. washThe combined organics were washed with brine (20 mL)
  5. customdried
  6. customThe residue was chromatographed (ISCO, 80 g Basic Alumina, 0-70% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-6f7e6093136c438c8d7631427c1c7a3e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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