Reaktion #502734

Reaktionsgleichung

Sodium borohydride

benzyl (3R)-3-[(3-nitroquinolin-4-yl)amino]butylcarbamate

sodium borohydride

→

benzyl (3R)-3-[(3-aminoquinolin-4-yl)amino]butylcarbamate

Ausbeute 93.7%

Lösungsmittel

methanol

methanol dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through a layer of CELITE filter agent
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe resulting brown solid was triturated with dichloromethane
4. 4
   Filtrationthe resulting mixture was filtered through a layer of CELITE filter agent
5. 5
   EinengenThe filtrate was concentrated under reduced pressure

Vorschrift

Sodium borohydride (110 mg, 2.8 mmol) was added to a solution of nickel (II) chloride hexahydrate (330 mg, 1.4 mmol) in 10 mL of methanol. A solution of benzyl (3R)-3-[(3-nitroquinolin-4-yl)amino]butylcarbamate (1.11 g, 2.81 mmol) in 20 mL of 1:1 methanol/dichloromethane was added, and the resulting dark mixture was stirred for 5 minutes at room temperature. Additional sodium borohydride was added in small portions until the reaction solution become colorless. The mixture was filtered through a layer of CELITE filter agent, and the filtrate was concentrated under reduced pressure. The resulting brown solid was triturated with dichloromethane, and the resulting mixture was filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure to provide 0.96 g of benzyl (3R)-3-[(3-aminoquinolin-4-yl)amino]butylcarbamate as a brown foam.

Quelle