Triethylamine → N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine

HRID 549110Notes

Reaction equation

HRID 549110 reaction equation
[Si:1]([O:8][C:9]([CH3:22])([CH3:21])[C@H:10]([NH2:20])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][C:32]=1[N+:41]([O-:43])=[O:42].C(OCC)(=O)C.C(Cl)Cl>C(Cl)Cl>[Si:1]([O:8][C:9]([CH3:22])([CH3:21])[C@H:10]([NH:20][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[CH:33][C:32]=1[N+:41]([O-:43])=[O:42])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 21226138Dichloromethane ethylacetateHCID 86624119(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine

Product 1

HCID 67156885N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine (5.85 g, 16.9 mmol) was dissolved in 200 mL of anhydrous CH2Cl2 and the mixture was stirred under N2. To this solution were added triethylamine (4.70 mL, 33.8 mmol) and 4-chloro-3-nitroquinoline (3.51 g, 16.9 mmol). The reaction mixture soon became bright yellow. After stirring for 3 days, the reaction mixture was concentrated under reduced pressure. The resulting yellow solid was partitioned between 200 mL H2O and 200 mL CH2Cl2. The layers were separated and the organic portion was washed with H2O and then brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting light brown oil was dissolved in about 200 mL of refluxing hexanes. A small amount of brown precipitate formed and was removed by filtration. The hexanes solution was concentrated to give a yellow solid. Chromatography (SiO2, 10% ethyl acetate/CH2Cl2) gave N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine (6.51 g) as a yellow solid.

Workup

  1. stirringAfter stirring for 3 days
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe resulting yellow solid was partitioned between 200 mL H2O and 200 mL CH2Cl2
  4. customThe layers were separated
  5. washthe organic portion was washed with H2O
  6. dry with materialThe organic portion was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting light brown oil was dissolved in about 200 mL of refluxing hexanes
  10. customA small amount of brown precipitate formed
  11. customwas removed by filtration
  12. concentrationThe hexanes solution was concentrated
  13. customto give a yellow solid

Sources & evidence

ORD record
ord-b91e205fcaea42ea949671cc981c6c73
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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