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

HRID 600801Notes

Reaction equation

HRID 600801 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 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)+.

Workup

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

Sources & evidence

ORD record
ord-665fd978ce95443581b733c9959d754b
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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