Sodium Hydroxide → 5,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

HRID 888095ノート

反応式

HRID 888095 の反応式
[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][C:6](=O)[NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O.C1COCC1>[CH3:1][C:2]1([CH3:14])[CH2:8][CH2:7][CH2:6][NH:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]1=2

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2 回HCID 570064745,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

生成物 1

HCID 574702555,5-dimethyl-2,3,4,5-tetrahydro-1H-1-benzazepine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

5,5-Dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1.5 g, 8.0 mmol) was dissolved into THF (20 ml) and cooled down to 0° C. LAH (0.5 g 60% in oil, 13 mmol) was added in portions. The reaction was heated to reflux for 2 h. TLC showed a new spot alongside staring lactam. Another 360 mg of LAH was added and the mixture was heated for 2 h. H2O was added until sizzling stopped followed by 2N NaOH. Stirred for 15 min at RT. Na2SO4 (3.8 g) was added and the mixture was stirred for 15 min followed by filtration over Celite®. Diluted with EtOAc and washed with H2O, dried (MgSO4), filtered and concentrated to give 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. temperaturethe mixture was heated for 2 h
  4. stirringthe mixture was stirred for 15 min
  5. filtrationfollowed by filtration over Celite®
  6. additionDiluted with EtOAc
  7. washwashed with H2O
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-9d0d82ddc0e04ca0a25d7e7b44c8bde8
出典データセット
uspto-grants-2012_08
特許番号
US08247556B2

反応ノート

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