Water → Phenyl 1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

HRID 1713527

반응식

HRID 1713527 반응식
[CH:1]1([C:4]2([CH:24]3[CH2:26][CH2:25]3)[CH:8]3[CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19]C=4)=[O:14])[CH2:11][CH2:12][N:7]3[C:6](=[O:23])[O:5]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.C(Cl)(=O)OC1C=CC=CC=1.O>C(O)C.[C].[Pd]>[CH:24]1([C:4]2([CH:1]3[CH2:3][CH2:2]3)[CH:8]3[CH2:9][N:10]([C:13]([O:15][C:16]4[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:14])[CH2:11][CH2:12][N:7]3[C:6](=[O:23])[O:5]2)[CH2:26][CH2:25]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 68422186(Phenylmethyl)1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

생성물 1

HCID 23121994Phenyl 1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate수율 88%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

(Phenylmethyl) 1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate (0.18 g, 0.50 mmol) was dissolved in ethanol (10 mL). 10% Palladium carbon (17 mg) was added thereto, and the mixture was stirred under hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through Celite, the Celite was washed with ethanol, and the filtrate was concentrated under reduced pressure. The resulting 1,1-dicyclopropyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one was dissolved in tetrahydrofuran (10 mL). Triethylamine (0.14 mL, 0.99 mmol) and phenyl chlorocarbonate (90 μL, 0.74 mmol) were added thereto, and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:1 to 1:1) and recrystallized from diisopropyl ether-hexane to obtain the title compound (0.15 g, 88% yield (phenylmethyl) 1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate).

후처리

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe Celite was washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe resulting 1,1-dicyclopropyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one was dissolved in tetrahydrofuran (10 mL)
  5. stirringthe mixture was stirred at room temperature for 2 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with an aqueous saturated sodium hydrogen carbonate solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=7:1 to 1:1)
  11. customrecrystallized from diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-819b64c8ae1848d08772408348fa667c
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795267B2

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