1-Fluoro-4-(isocyanatomethyl)benzene → 1,1-Dicyclopropyl-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide

HRID 1713526

反応式

HRID 1713526 の反応式
C1(COC([N:11]2[CH2:16][CH2:15][N:14]3[C:17](=[O:26])[O:18][C:19]([CH:23]4[CH2:25][CH2:24]4)([CH:20]4[CH2:22][CH2:21]4)[CH:13]3[CH2:12]2)=O)C=CC=CC=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([CH2:32][N:33]=[C:34]=[O:35])=[CH:30][CH:29]=1>C(O)C.[C].[Pd]>[CH:23]1([C:19]2([CH:20]3[CH2:22][CH2:21]3)[CH:13]3[CH2:12][N:11]([C:34]([NH:33][CH2:32][C:31]4[CH:30]=[CH:29][C:28]([F:27])=[CH:37][CH:36]=4)=[O:35])[CH2:16][CH2:15][N:14]3[C:17](=[O:26])[O:18]2)[CH2:25][CH2:24]1

参加物

5

反応物 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 68422186(Phenylmethyl)1,1-dicyclopropyl-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxylate

生成物 1

HCID 231219031,1-Dicyclopropyl-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide収率 87%

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). (4-Fluoro)benzyl isocyanate (0.25 mL, 2.0 mmol) was added thereto, and the mixture was stirred at 50° C. for 4 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:4) to obtain the title compound (0.16 g, 87% yield from (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 50° C. for 4 hours
  6. concentrationThe reaction solution was concentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1 to 1:4)

出典と根拠

ORDレコード
ord-4624d882f6804bfc8a6e39a5595b56cc
出典データセット
uspto-grants-2010_09
特許番号
US07795267B2

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