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

HRID 63075

반응식

HRID 63075 반응식
[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

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 9883512zinc(II)iodide촉매HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-060b901605a7488ead9bd01c7620fa71
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

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