Water → HCID 70976107、化合物

HRID 455270ノート

反応式

HRID 455270 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.[CH2:24]([CH:27]1[CH2:29][O:28]1)[CH2:25][CH3:26].O>C1COCC1>[OH:28][CH:27]([CH2:24][CH2:25][CH3:26])[CH2:29][O: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:19])[F:20])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1

参加物

6

反応物 4

HCID 962WaterHCID 13853Oxirane, 2-propyl-HCID 24758Sodium hydrideHCID 70976331HCID 70976331、化合物

生成物 1

HCID 70976107HCID 70976107、化合物収率 26%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (25 mg, 70% in oil, 0.7 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) (300 mg, 1 mmol) in anhydrous THF (10 mL), the mixture was stirred at room temperature for 0.5 hour, then 2-propyloxirane (300 mg, 3.5 mmol) was added to the solution, the mixture was stirred at 75° C. overnight in a sealed tube. The mixture was cooled and poured into water (50 mL), extracted with ethyl acetate (3×30 mL), the organic layers was combined and washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=4:1) to yield 100 mg (26%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.62 (d, 2H, J=8.7 Hz), 7.19 (d, 2H, J=8.7 Hz), 4.20 (t, 1H, J=5.7 Hz), 4.09-4.00 (m, 3H), 3.82-3.74 (m, 2H), 3.52-3.43 (m, 1H), 3.37-3.18 (m, 2H), 2.26-2.10 (m, 2H), 1.60-1.38 (m, 5H), 0.96 (t, 3H, J=6.9 Hz); LC-MS: 389.1 [M+1]+.

後処理

  1. stirringthe mixture was stirred at 75° C. overnight in a sealed tube
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (eluting with petroleum ether/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-f3b4fc96d1024f92b33ea7028d0bc4e2
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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