Imidazole → HCID 178455374、化合物

HRID 452961ノート

反応式

HRID 452961 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([OH:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([O:14][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178521634HCID 178521634、化合物

生成物 1

HCID 178455374HCID 178455374、化合物収率 73.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of cis-3-(benzyloxymethyl)cyclobutanol (Albany Molecular, 1.0 g, 5.2 mmol) in CH2Cl2 (20 mL) was added imidazole (0.71 g, 10.4 mmol), DMAP (64 mg, 0.52 mmol) and tert-butyldimethylsilylchloride (TBSCl) (1.6 g, 10.4 mmol). This mixture was stirred at ambient temperature for 16 h, quenched with saturated, aqueous NH4Cl (5 mL) and diluted with EtOAc (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/EtOAc) to give the title compound (1.15 g, 3.8 mmol, 72% yield). MS (DCI/NH3) m/z 307 (M+H)+.

後処理

  1. customquenched with saturated, aqueous NH4Cl (5 mL)
  2. additiondiluted with EtOAc (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified via column chromatography (SiO2, 50% hexanes/EtOAc)

出典と根拠

ORDレコード
ord-f5f9a21780be44ee94d657912589e32e
出典データセット
uspto-grants-2013_07
特許番号
US08492371B2

反応ノート

読み込み中…