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

HRID 1713527

反応式

HRID 1713527 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-819b64c8ae1848d08772408348fa667c
出典データセット
uspto-grants-2010_09
特許番号
US07795267B2

関連ノート

読み込み中…