Tetrabutylammonium Fluoride → tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylate

HRID 2213053ノート

反応式

HRID 2213053 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC[CH2:21][N:22]([CH2:30][C:31]1[N:32]([CH2:36]OCC[Si](C)(C)C)[CH:33]=[CH:34][N:35]=1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>O1CCCC1>[N:35]1[CH:34]=[CH:33][N:32]2[CH2:36][CH2:21][N:22]([C:23]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:29])[CH2:30][C:31]=12

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium Fluoride2 回HCID 695594341,1-Dimethylethyl N-(2-Chloroethyl)-N-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-ylmethyl)carbamate

生成物 1

HCID 21955306tert-Butyl 5,6-dihydroimidazo(1,2-a)pyrazine-7(8H)-carboxylate収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Tetrabutylammonium fluoride (1M in tetrahydrofuran, 7.1 mL, 7.1 mmol) was added to a solution of 1,1-dimethylethyl N-(2-chloroethyl)-N-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-ylmethyl)carbamate (Description 162, 2.52 g, 6.5 mmol) in tetrahydrofuran (50 mL) and the mixture was heated under reflux for 1.5 hours. Further tetrabutylammonium fluoride (1M in tetrahydrofuran, 7.1 mL, 7.1 mmol) was added and the mixture was heated under reflux for 20 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/MeOH (97:3), to give the title compound (505 mg, 35%). m/z (ES+) 224 (M+1).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 20 hours
  5. temperatureThe mixture was cooled
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH (97:3)

出典と根拠

ORDレコード
ord-a962892eda4945aeadf8444726730051
出典データセット
uspto-grants-2006_09
特許番号
US07105507B2

反応ノート

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