Reaktion #308754

Reaktionsgleichung

(2S)-1-(Benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-amine

Triethylamine

4-chloro-3-nitroquinoline

→

N-[(1S)-2-(benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl]-3-nitroquinolin-4-amine

Ausbeute 73.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated
2. 2
   Sonstigethe resulting material was partitioned between 50 mL of CH2Cl2 and 50 mL of saturated NaHCO3 solution
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe organic portion was washed with H2O and brine
5. 5
   TrocknenThe organic portion was dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure

Vorschrift

(2S)-1-(Benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-amine (1.55 g, 5.25 mmol) was dissolved in 60 mL of dry CH2Cl2. Triethylamine (1.46 mL, 10.5 mmol) and 4-chloro-3-nitroquinoline (1.09 g, 5.25 mmol) were then added and the reaction was stirred under N2 for 2 days. The reaction mixture was then concentrated and the resulting material was partitioned between 50 mL of CH2Cl2 and 50 mL of saturated NaHCO3 solution. The layers were separated and the organic portion was washed with H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 0-10% ethyl acetate/CH2Cl2) gave 1.81 g of N-[(1S)-2-(benzyloxy)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl]-3-nitroquinolin-4-amine as a yellow solid.

Quelle