Aluminium lithium hydride → (R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzylamine

HRID 1191081ノート

反応式

HRID 1191081 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@@H:8]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[N:18]=1)[C:9]([F:12])([F:11])[F:10]>C1COCC1>[CH3:7][C@@H:8]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=2)[N:18]=1)[C:9]([F:10])([F:12])[F:11]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86624159(R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzonitrile

生成物 1

HCID 59828830(R)-4-[2-(1-Methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzylamine収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Add a solution of 1M lithium aluminum hydride in THF (12 mL, 12 mmol) dropwise to an ice-cooled solution of (R)-4-[2-(1-methyl-2,2,2-trifluoroethylamino)-thiazol-4-yl]-benzonitrile in anhydrous THF (10 mL). Heat to reflux for 1 h, cool to room temperature, quench by slow addition of water (12 mL), ether (50 mL), 1N NaOH (12 mL) and additional water (36 mL). Add EtOAc (50 mL), stir vigorously for 20 min and filter over a bed of Celite®. Dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain the title compound (765 mg, 64%). MS (ES+) m/z: 302 (M+H)+.

後処理

  1. temperatureHeat
  2. temperatureto reflux for 1 h
  3. customquench by slow addition of water (12 mL), ether (50 mL), 1N NaOH (12 mL) and additional water (36 mL)
  4. filtrationfilter over a bed of Celite®
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-518555e7399a4df282d3260dc20c0cd4
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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