Hydrochloric Acid → t-Butyl 3-[N-[2-(1-adamantyl)ethyl]amino]propionate hydrochloride

HRID 11435

반응식

HRID 11435 반응식
[ClH:1].[C:2]12([CH2:12][CH2:13][NH2:14])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(N(CC)CC)C.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24].Cl.C(OCC)(=O)C>C(O)C>[ClH:1].[C:2]12([CH2:12][CH2:13][NH:14][CH2:24][CH2:23][C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:9][CH:8]3[CH2:7][CH:6]([CH2:5][CH:4]([CH2:10]3)[CH2:3]1)[CH2:11]2

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 15458tert-Butyl acrylateHCID 27711382-(Adamantan-1-yl)ethan-1-amine hydrochloride

생성물 1

HCID 21974130t-Butyl 3-[N-[2-(1-adamantyl)ethyl]amino]propionate hydrochloride수율 23%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-(1-Adamantyl)ethylamine hydrochloride (1.0 g, 4.6 mmol) was dissolved in ethanol (10 ml), and triethylamine (0.65 ml, 4.6 mmol) and t-butyl acrylate (0.75 ml, 5.1 mmol) were added to the solution under ice-cooling. Then, the temperature was raised to room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, a 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers were separated. The ethyl acetate layer was washed with water (50 ml) and a saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate. The ethyl acetate layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography. The resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml), and a 4 N solution of hydrogen chloride in ethyl acetate (1.0 ml, 4.0 mmol) was added thereto to precipitate a solid. This solid was filtered off with diethyl ether to give 0.33 g (23%) of the titled compound.

후처리

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 1 N aqueous sodium hydroxide solution (30 ml) and ethyl acetate (50 ml) were added to the residue, and layers
  4. customwere separated
  5. washThe ethyl acetate layer was washed with water (50 ml)
  6. dry with materiala saturated aqueous sodium chloride solution (50 ml) successively and dried over anhydrous magnesium sulfate
  7. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  8. customthe concentrate was purified by silica gel column chromatography
  9. dissolutionThe resulting oily matter (0.50 g, 1.6 mmol) was dissolved in diethyl ether (20 ml)
  10. customto precipitate a solid
  11. filtrationThis solid was filtered off with diethyl ether

출처 및 근거

ORD 기록
ord-a9db451ed9c34a17965ac9e79daed3a9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098226B2

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