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Potassium Carbonate → 3-(trifluoromethoxy)phenyl (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 1184588
ノート
印刷プレビュー

反応式

HRID 1184588 の反応式
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:22][N:14]4[CH2:15][CH2:16][N:17]([C:19](Cl)=[O:20])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:22][N:14]4[CH2:15][CH2:16][N:17]([C:19]([O:32][C:28]5[CH:29]=[CH:30][CH:31]=[C:26]([O:25][C:24]([F:23])([F:33])[F:34])[CH:27]=5)=[O:20])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27332613-(Trifluoromethoxy)phenolHCID 86680508(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazine-2(1H)-carbonyl chloride

生成物 1

HCID 866805093-(trifluoromethoxy)phenyl (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]-hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of the product from Example 114A (26 mg, 0.081 mmol) and 3-(trifluoromethoxy)phenol (14 mg, 0.081 mmol) in anhydrous N,N-dimethylformamide (0.8 mL) was added potassium carbonate (17 mg, 0.12 mmol), and the resulting mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water, and the organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 0.89-1.01 (m, 4 H), 1.83-2.09 (m, 3 H), 2.30-2.59 (m, 3 H), 2.60-2.93 (m, 1 H), 2.97-3.38 (m, 2 H), 3.76 (dd, J=9.9, 6.7 Hz, 1 H), 4.15-4.29 (m, 1 H), 4.30-4.45 (m, 1 H), 5.38 (q, J=5.8 Hz, 1 H), 7.00-7.13 (m, 3 H), 7.37 (t, J=8.1 Hz, 1 H), 7.95 (d, J=1.2 Hz, 1 H), 8.04 (d, J=1.2 Hz, 1 H); MS (ESI) m/z 465.0 (M+H)+.

後処理

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-d2c1de8ac4394261aa2be8712566b57e
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08669255B2

反応ノート

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