Water → (6R,7aS)-6-(1-Phenyl-ethoxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

HRID 455261ノート

反応式

HRID 455261 の反応式
[H-].[Na+].[OH:3][C@H:4]1[CH2:23][N:7]2[C:8](=[O:22])[N:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1.Br[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26].O>C1COCC1>[C:27]1([CH:25]([O:3][C@H:4]2[CH2:23][N:7]3[C:8](=[O:22])[N:9]([C:11]4[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:13][CH:12]=4)[CH2:10][C@@H:6]3[CH2:5]2)[CH3:26])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 962WaterHCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 70976331(6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one

生成物 1

HCID 70976297(6R,7aS)-6-(1-Phenyl-ethoxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (70% in oil, 7 mg, 0.2 mmol) was added to a solution of (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 1, step e) (50 mg, 0.165 mmol) and (1-Bromo-ethyl)-benzene (40 mg, 0.21 mmol) in anhydrous THF (10 mL), the mixture was refluxed overnight. The mixture was cooled and poured into water (20 mL), extracted with ethyl acetate (3×20 mL), the organic layers was combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=7:1) to give 20 mg (30%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.57 (dd, 2H, J1=9.0 Hz, J2=1.8 Hz), 7.38-7.26 (m, 5H), 7.17 (d, 2H, J=9.0 Hz), 4.52-4.42 (m, 1H), 4.12-3.84 (m, 4H), 3.71-3.61 (m, 1H), 3.27-3.06 (m, 1H), 2.28-2.02 (m, 1H), 1.49-1.37 (m, 4H); LC-MS: 407.0 [M+1]+.

後処理

  1. temperaturethe mixture was refluxed overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=7:1)

出典と根拠

ORDレコード
ord-dc3fb0301d6b464585a3caeb85e7403e
出典データセット
uspto-grants-2013_07
特許番号
US08497288B2

反応ノート

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