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

HRID 221526Notes

Reaction equation

HRID 221526 reaction equation
[CH3:1][CH:2]([CH3:20])[C@H:3]([NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH2:4][OH:5].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:21]([O:5][CH2:4][C@@H:3]([NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH:2]([CH3:20])[CH3:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67156854(2S)-3-methyl-2-[(3-nitroquinolin-4-yl)amino]butan-1-ol

Product 1

HCID 67157210N-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amineYield 97.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
56 °C

Procedure

(2S)-3-Methyl-2-[(3-nitroquinolin-4-yl)amino]butan-1-ol (3.97 g, 14.4 mmol) was dissolved in 15 mL of dry pyridine and treated with tert-butyldimethylsilyl chloride (2.40 g, 15.9 mmol) and a catalytic amount of 4-(dimethylamino)pyridine (DMAP) (176 mg, 1.44 mmol). The reaction mixture was stirred under N2 and heated to 56° C. After 2 days, the reaction mixture was concentrated under reduced pressure. The resulting solid was partitioned between 100 mL of H2O and 100 mL of ethyl acetate. The layers were separated and the organic portion was washed with H2O and brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 20% ethyl acetate/hexanes) gave N-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine (5.46 g) as a yellow syrup.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting solid was partitioned between 100 mL of H2O and 100 mL of ethyl acetate
  3. customThe layers were separated
  4. washthe organic portion was washed with H2O and brine
  5. dry with materialThe organic portion was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bd36c6907f9492c91556a3d27313687
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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