Potassium Carbonate → cis-2-[(3-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1269948ノート

反応式

HRID 1269948 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:9]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10]1)#[N:8].[OH-].[Na+].Cl.C(OCC)C.C(=O)([O-])[O-].[K+].[K+].C([O:32][C:33]([C:35]1[CH:45]=[CH:44][CH:43]=[C:37]2C(N[C:41](=[O:42])[C:36]=12)=O)=O)C>O1CCCC1.O.C(#N)C>[OH:15][C@@H:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([CH2:7][N:8]2[C:33](=[O:32])[C:35]3[C:36](=[CH:37][CH:43]=[CH:44][CH:45]=3)[C:41]2=[O:42])[CH2:10]1

参加物

10

反応物 6

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 10953452Ether hydrochlorideHCID 128412163-Oxocyclohexane-1-carbonitrileHCID 21226445Aluminium lithium hydrideHCID 22254400Ethoxycarbonylphthalimide

生成物 1

HCID 69433420cis-2-[(3-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione収率 40%

試薬・触媒・溶媒 3

HCID 962Water溶媒3 回HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere, lithium aluminum hydride (92 mg, 2.44 mmol) was added to a solution of 1-cyanocyclohexan-3-one (100 mg, 0.812 mmol) in tetrahydrofuran (2 ml) at room temperature, and the resulting mixture was refluxed. After 5 hours, water, an aqueous sodium hydroxide solution and water were added in that order to the reaction solution, and the resulting mixture was filtered under reduced pressure. Thereafter, 1M-hydrochloric acid-diethyl ether (974 μl, 0.974 mmol) was added to the filtrate. The resulting mixture was concentrated under reduced pressure, and to an aqueous solution (4 ml) of the resulting residue were added potassium carbonate (202 mg, 1.46 mmol), ethoxycarbonylphthalimide (196 mg, 0.893 mmol) and acetonitrile (1 ml) at room temperature. After 21 hours, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) and purified again by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain cis-2-[(3-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione (83.5 mg, 40%, cis:trans=12:1).

後処理

  1. temperaturethe resulting mixture was refluxed
  2. filtrationthe resulting mixture was filtered under reduced pressure
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. waitAfter 21 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe organic layer dried
  8. concentrationwas concentrated under reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  10. custompurified again by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

出典と根拠

ORDレコード
ord-00c24a33d2ac47298f6711ddc65bc0ab
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

反応ノート

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