Trimethylsilyl iodide → [1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalen-1-yl]methyl Isopropylcarbamate

HRID 494664Notes

Reaction equation

HRID 494664 reaction equation
[CH:1]([NH:4][C:5](=[O:26])[O:6][CH2:7][C:8]1([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[CH:10]=[C:9]1[O:19]C)([CH3:3])[CH3:2].I[Si](C)(C)C>C(#N)C>[CH:1]([NH:4][C:5](=[O:26])[O:6][CH2:7][C:8]1([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[CH2:10][C:9]1=[O:19])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 68874679[2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl Isopropylcarbamate

Product 1

HCID 68871669[1-(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydronaphthalen-1-yl]methyl IsopropylcarbamateYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 180B (32 mg, 0.09 mmol) in acetonitrile (1 mL) was added iodotrimethylsilane (TMSI) (19 μL, 0.13 mmol). The reaction solution was stirred at room temperature for 3 h. After which, additional 1.5 equivalents of TMSI (19 μL) were added and stirring was continued for 2 h. The solution was quenched with water (2 mL) and extracted with ethyl acetate (2× 1 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (70% ethyl acetate/hexane) afforded product as a white foam (24 mg, 77%). MS m/z 346.0 (M+H)+

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe solution was quenched with water (2 mL)
  4. extractionextracted with ethyl acetate (2× 1 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b53c32fc407f4a27840efc2a1ef53ebc
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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