Potassium Carbonate → tert-Butyl 4-(3-oxo-3,4-dihydroisoquinolin-2(1H)-yl)piperidine-1-carboxylate

HRID 132209

반응식

HRID 132209 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18]C)=O.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1>C(#N)C>[O:18]=[C:16]1[CH2:15][C:10]2[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][N:20]1[CH:21]1[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 9855748Methyl 2-[2-(chloromethyl)phenyl]acetate

생성물 1

HCID 59731897tert-Butyl 4-(3-oxo-3,4-dihydroisoquinolin-2(1H)-yl)piperidine-1-carboxylate수율 40%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Potassium carbonate (1.4 g, 10 mmol) was added to a solution of methyl 2-(2-(chloromethyl)phenyl)acetate (940 mg, 4.7 mmol) in acetonitrile (20 mL). 4-Amino-N-Boc-piperidine (1.13 g, 5.6 mmol) was added to the mixture. Reaction was heated at reflux for 1 hour. Mixture was cooled to room temperature and then filtered over celite. Filtrate was concentrated in vacuo. Residue was treated with toluene (29 mL). Acetic acid (1.5 ml) was added to the mixture. Reaction was heated at reflux for 2 hours. Mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed successively with aqueous sodium bicarbonate (2×30 mL), 1N hydrochloric acid (30 mL), and brine (20 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Silica gel chromatography gave the title compound as lightly colored oil in 40% yield. MS m/e (M+H)+=331.2.

후처리

  1. customReaction
  2. temperaturewas heated
  3. temperatureat reflux for 1 hour
  4. filtrationfiltered over celite
  5. concentrationFiltrate was concentrated in vacuo
  6. additionResidue was treated with toluene (29 mL)
  7. additionAcetic acid (1.5 ml) was added to the mixture
  8. customReaction
  9. temperaturewas heated
  10. temperatureat reflux for 2 hours
  11. concentrationMixture was concentrated in vacuo
  12. additionResidue was treated with ethyl acetate (50 mL)
  13. washMixture was washed successively with aqueous sodium bicarbonate (2×30 mL), 1N hydrochloric acid (30 mL), and brine (20 mL)
  14. dry with materialOrganic layer was dried (magnesium sulfate)
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7f3c353e3ba44efd995d03b8bbeced21
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384930B2

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