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

HRID 18403

반응식

HRID 18403 반응식
[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

참가 물질

7

반응물 4

HCID 8471Triethylamine2회HCID 729234-PyridinepropanolHCID 676246Di(succinimido) carbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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. After separation, the organic layer was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dried under reduced pressure and dissolved in anhydrous methylene chloride (10 ml). Next, a solution of 2-(1adamantyl)-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 dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (1.54 g, 97%) as an oily matter.

후처리

  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. customAfter separation
  4. washthe organic layer was washed with a saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried 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 dried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4da1186c1baa467faac6246b1a798527
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741346B2

연결된 노트

불러오는 중…