Reaktion #2507894

Reaktionsgleichung

potassium

2-methoxy-4-nitrophenol

t-butyl 2-chloroethylcarbamate

K2CO3

NaI

→

tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionAfter dilution with H2O, the mixture was extracted 4× with CH2Cl2
2. 2
   WaschenThe combined organic layers were washed 2× with aq, K2CO3
3. 3
   Trocknenwith brine prior to drying over Na2SO4
4. 4
   SonstigeAfter removal of the solvent under vacuum
5. 5
   Sonstigethe residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2
6. 6
   Waschento elute 870 mg of nitrophenyl ether
7. 7
   Sonstigewas carried forward, without further purification

Vorschrift

A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq, K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward, without further purification.

Quelle