Imidazole → 7-{[Tert-butyl(dimethyl)silyl]oxy}-5,6,7,8-tetrahydronaphthalen-1-amine

HRID 1662131노트

반응식

HRID 1662131 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2.[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1>ClCCl>[Si:17]([O:12][CH:9]1[CH2:10][C:11]2[C:2]([NH2:1])=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:7][CH2:8]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

생성물 1

HCID 587341927-{[Tert-butyl(dimethyl)silyl]oxy}-5,6,7,8-tetrahydronaphthalen-1-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of Example 1F (2.33 g, 14.3 mmol), tert-butylchlorodimethylsilane (2.6 g, 17.2 mmol) and imidazole (2.9 g, 42.3 mmol) in dichloromethane (40 mL) were stirred at ambient temperature overnight. The mixture was then washed several times with water and once with brine. The organic layer was separated and dried over anhydrous sodium sulfate. Filtration and concentration afforded the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 0.09 (s, 6H), 0.88 (s, 9H), 1.63 (m, 1H), 1.82 (m, 1H), 2.24 (m, 1H), 2.75 (m, 3H), 4.11 (m, 1H), 4.7 (br s, 2H), 6.28 (d, J=7.4 Hz, 1H), 6.42 (d, J=7.8 Hz, 1H), 6.77 (dd, J=7.8, 7.4 Hz, 1H). MS (ESI) m/z 278 (M+H)+.

후처리

  1. washThe mixture was then washed several times with water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration

출처 및 근거

ORD 기록
ord-552b115bca2b487cb280b97435a3a791
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030504B2

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