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

HRID 132342

反応式

HRID 132342 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c62aec5ca2494010950b6f1b2c45d280
出典データセット
uspto-grants-2008_06
特許番号
US07384931B2

関連ノート

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