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Hydrochloric Acid → tert-Butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088887
ノート
印刷プレビュー

反応式

HRID 2088887 の反応式
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:12]=[C:11]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.O1CCCC1.Cl>C(OCC)(=O)C>[OH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[N:12]=[C:11]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]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 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67954713tert-Butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 67113226tert-Butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate収率 79.5%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

Combine tert-butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (6.88 g, 14.84 mmol), tetrahydrofuran (136 mL) and 1 N aqueous hydrochloric acid (25 mL). Stir the reaction at room temperature overnight. Dilute with ethyl acetate and wash with saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate. Extract the combined aqueous layers with 9:1 dichloromethane:isopropyl alcohol. Dry the combined organic layers over anhydrous sodium sulfate, filter, and concentrate in vacuo. Purify by silica gel chromatography, eluting with hexanes to 50% ethyl acetate in hexanes to ethyl acetate to 10% methanol in ethyl acetate to 10% methanol in dichloromethane, to give the title compound as a white solid (4.48 g, 79%). MS (ES) m/z=380 [M]+.

後処理

  1. customthe reaction at room temperature overnight
  2. washwash with saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate
  3. extractionExtract the combined aqueous layers with 9:1 dichloromethane
  4. dry with materialDry the combined organic layers over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by silica gel chromatography
  8. washeluting with hexanes to 50% ethyl acetate in hexanes to ethyl acetate to 10% methanol in ethyl acetate to 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-578bde80f9ee481ebbaec8fba76df9e3
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08436002B2

反応ノート

読み込み中…

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