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

HRID 1803749Notes

Reaction equation

HRID 1803749 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-8c8d2597a0ec4fb0aa5ddc12144bc15a
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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