Aluminium lithium hydride → (1-Benzylazepan-3-yl)methanol

HRID 479823노트

반응식

HRID 479823 반응식
C[O:2][C:3]([CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=O)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH3:7].[CH2:12]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:5]([CH2:3][OH:2])[CH2:6]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

생성물 2

HCID 222AmmoniaHCID 21901990(1-Benzylazepan-3-yl)methanol수율 117.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-Benzyl-2-oxo-azepan-2-carboxylic acid methyl ester (143) (0.2154 g, 0.8243 mmol) dissolved in anhydrous THF (2.9 mL) was added to a stirring suspension of LiAlH4 in THF (1.5 mL) over approx. 1.5 hours. The reaction mixture was stirred overnight. The reaction was judged complete by TLC and was quenched by the sequential addition of H2O (0.4 mL), then 2N NaOH (1.0 mL) and H2O (0.4 mL). The mixture was stirred at room temperature for 30 minutes, then was filtered, dried with Na2SO4, and concentrated in vacuo. Crude material was purified by automated silica gel chromatography with 15:85:5 CH2Cl2:Hexanes:2N NH3 in EtOH to obtain 0.1062 g (59%) of pure (1-benzyl-azepan-3-yl)-methanol (144). 1H NMR (CDCl3) 7.40-7.23 (5H, m), 3.65 (2H, s), 3.54 (1H, dd, J=10.4, 3.5 Hz), 3.43 (1H, dd, J=10.4, 5.4 Hz), 2.82 (1H, J=13.3, 3.1 Hz), 2.77 (2H, m), 2.44 (1H, ddd, J=12.2, 8.6, 3.3 Hz), 1.90-1.45 (6H, m) ppm. 13C NMR (CDCl3, 75 MHz) 139.14, 128.97, 128.14, 126.91, 67.20, 63.85, 58.49, 56.87, 39.59, 29.68, 29.43, 25.23 ppm. LRMS: 219.64.

후처리

  1. customwas quenched by the sequential addition of H2O (0.4 mL)
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. filtrationwas filtered
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrude material was purified by automated silica gel chromatography with 15:85:5 CH2Cl2

출처 및 근거

ORD 기록
ord-3581611d190b4dc098ab21c7d17e8b0b
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645980B1

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