6-Methoxy-alpha-tetralone → 1-(Aminomethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 63075

反応式

HRID 63075 の反応式
[Si]([C:5]#[N:6])(C)(C)C.[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O.[I-].[Zn+2].[I-].O>[NH2:6][CH2:5][C:15]1([OH:19])[C:16]2[C:11](=[CH:10][C:9]([O:8][CH3:7])=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH2:14]1

参加物

10

反応物 4

HCID 141126-Methoxy-alpha-tetraloneHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 131975891-(Aminomethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol収率 68.4%

試薬・触媒・溶媒 5

HCID 9883512zinc(II)iodide触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
60 °C

実験手順

TMS-cyanide (8.52 mL, 68.1 mmol) was added to a solution of 6-methoxy-1-tetralone (6.0 g, 34 mmol) in toluene (50 mL). A trace amount (˜20 mg) of zinc iodide was added, and the reaction was stirred at 60° C. for 16 hours. The solution was cooled to rt and diluted with THF (30 mL). This was added to a mixture of lithium aluminum hydride (2.58 g) in THF (50 mL), and the reaction mixture was heated at 42° C. for 2 h. The reaction was cooled to rt. EtOAc (10 mL) was slowly added, and the reaction stirred 30 min. Water (2 mL) and then 5N NaOH (1 mL) were slowly added, and the reaction stirred 1 h. The reaction mixture was diluted with EtOAc (100 mL), dried (MgSO4), and filtered through Celite. Purification by silica gel chromatography (10-20% MeOH/DCM) gave 4.82 g of 1-(aminomethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol as a clear oil.

後処理

  1. temperatureThe solution was cooled to rt
  2. temperaturethe reaction mixture was heated at 42° C. for 2 h
  3. temperatureThe reaction was cooled to rt
  4. stirringthe reaction stirred 30 min
  5. stirringthe reaction stirred 1 h
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through Celite
  8. customPurification by silica gel chromatography (10-20% MeOH/DCM)

出典と根拠

ORDレコード
ord-060b901605a7488ead9bd01c7620fa71
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

関連ノート

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