Aluminium lithium hydride → 3,3-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine

HRID 340821ノート

反応式

HRID 340821 の反応式
Br[C:2]1[CH:15]=[N:14][C:5]2[NH:6][C:7](=O)[C:8]([CH3:12])([CH3:11])[NH:9][CH2:10][C:4]=2[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:11][C:8]1([CH3:12])[CH2:7][NH:6][C:5]2[N:14]=[CH:15][CH:2]=[CH:3][C:4]=2[CH2:10][NH:9]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 594569147-Bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one

生成物 1

HCID 593328723,3-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine収率 134.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 7-bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one (0.50 g, 1.8 mmol) in THF (15 mL) was cooled in an ice bath and treated dropwise with LiAlH4 (4.1 mL of a 1.0 M solution in THF, 4.1 mmol). After stirring for 30 mm, the ice bath was removed and the solution was allowed to warm to room temperature. After heating to reflux overnight, the mixture was cooled in an ice bath. The reaction was quenched sequentially with H2O (0.15 mL), 15% NaOH (0.15 mL) and H2O (0.45 ml). After 5 min, the ice bath was removed and the mixture was stirred at room temperature for 1.5 h. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to give the title compound (0.43 g; quantitative) as a white solid; 1H NMR (300 MHz, CDCl3) δ7.90 (dd, J=4.9, 1.5 Hz, 1H), 7.17 (d, J=7.2 Hz, 1H), 6.61 (dd, J=7.2, 4.9 Hz, 1H), 4.85 (br s, 1H), 3.91 (s, 2H), 3.22 (d, J=4.5 Hz, 2H), 2.39 (br s, 1H), 1.20 (s, 6H); MS (ESI) m/e 178 (M+H)+.

後処理

  1. temperaturewas cooled in an ice bath
  2. customthe ice bath was removed
  3. temperatureAfter heating
  4. temperatureto reflux overnight
  5. temperaturethe mixture was cooled in an ice bath
  6. customThe reaction was quenched sequentially with H2O (0.15 mL), 15% NaOH (0.15 mL) and H2O (0.45 ml)
  7. customthe ice bath was removed
  8. stirringthe mixture was stirred at room temperature for 1.5 h
  9. filtrationThe mixture was filtered through Celite
  10. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-4a6a5d2bc4bf41639e31e8f55997d512
出典データセット
uspto-grants-2014_11
特許番号
US08895545B2

反応ノート

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