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

HRID 1785564노트

반응식

HRID 1785564 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 the product of Example 18A (2.33 g, 14.3 mmol), tert-butylchlorodimethylsilane (2.6 g, 17.2 mmol), and imidazole (2.9 g, 42.3 mmol) was stirred in 40 mL of dichloromethane at rt overnight. The mixture was then washed several times with water and once with brine. Drying over Na2SO4, filtered and evaporation afforded the product as a dark purple oil, 2.6 g (65%). 1H NMR (DMSO-d6) δ 6.77 (dd, J=7.8, 7.4 Hz, 1H), 6.42 (d, J=7.8 Hz, 1H), 6.28 (d, J=7.4 Hz, 1H), 4.7 (br s, 2H), 4.11 (m, 1H), 2.75 (m, 3H), 2.24 (m, 1H), 1.82 (m, 1H), 1.63 (m, 1H), 0.88 (s, 9H), 0.09 (s, 6H); MS (ESI+) m/z 278 (M+H)+.

후처리

  1. washThe mixture was then washed several times with water
  2. dry with materialDrying over Na2SO4
  3. filtrationfiltered
  4. customevaporation

출처 및 근거

ORD 기록
ord-8b411211982241daabf946e933b4fdea
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504520B2

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