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

HRID 1035489Notes

Reaction equation

HRID 1035489 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-4ecdfbb6cb904bbf8a59b3c5c1b1b524
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

Loading…