Triethylamine → 3-(4-Pyridyl)propyl n-[2-(1-adamantyl)ethyl]-n-pentylcarbamate

HRID 11466

反応式

HRID 11466 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.C(N(CC)CC)C.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:20](=[O:21])C1.Cl.[C:37]12([CH2:47][CH2:48][NH:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2>C(#N)C.C(Cl)Cl>[C:37]12([CH2:47][CH2:48][N:49]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:20](=[O:21])[O:10][CH2:9][CH2:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:44][CH:43]3[CH2:42][CH:41]([CH2:40][CH:39]([CH2:45]3)[CH2:38]1)[CH2:46]2

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 729234-PyridinepropanolHCID 676246Di(succinimido) carbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

生成物 1

HCID 219741273-(4-Pyridyl)propyl n-[2-(1-adamantyl)ethyl]-n-pentylcarbamate収率 97%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Pyridinepropanol (528 mg, 3.85 mmol) was dissolved in acetonitrile (20 ml) at room temperature, and then triethylamine (1.61 ml, 11.6 mmol) was added to the solution. Further, N,N-disuccinimidyl carbonate (1.48 g, 5.87 mmol) was added to the mixture, and the whole was stirred for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate (100 ml) and a saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the residue. Layers were separated, and the obtained organic layer was washed with a saturated aqueous sodium chloride solution (50 ml). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was dried under reduced pressure and dissolved in anhydrous methylene chloride (10 ml). Then, a solution of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1) (1.32 g, 4.62 mmol) and triethylamine (0.80 ml, 5.7 mmol) in methylene chloride (90 ml) was added thereto, and the mixture was stirred for 1.5 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and a saturated aqueous sodium chloride solution (50 ml) successively, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 1.54 g (97%) of the titled compound as an oily matter.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate (100 ml)
  2. additiona saturated aqueous sodium hydrogencarbonate solution (50 ml) were added to the residue
  3. customLayers were separated
  4. washthe obtained organic layer was washed with a saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was dried under reduced pressure
  8. dissolutiondissolved in anhydrous methylene chloride (10 ml)
  9. stirringthe mixture was stirred for 1.5 hours
  10. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution (50 ml)
  11. dry with materiala saturated aqueous sodium chloride solution (50 ml) successively, and the organic layer was dried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-14e89434f0004fa7ac104f39d66973e3
出典データセット
uspto-grants-2006_08
特許番号
US07098226B2

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