Reaktion #162615

Reaktionsgleichung

8,8′-(2-(4-nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane)

8,8′-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane)

→

title compound

Ausbeute 86.1%

4-(4,6-Di(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)pyrimidin-2-yl)aniline

Ausbeute 86.1%

Lösungsmittel

2-propanol

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 250 mL round-bottomed flask was placed
2. 2
   FiltrationThe mixture was filtered over Celite™
3. 3
   Waschenrinsed with dichloromethane
4. 4
   Einengenconcentrated
5. 5
   workup.ADDITIONThe crude product was added to a silica gel column
6. 6
   Waschenwas eluted with ethyl acetate in hexanes (40-60%)
7. 7
   EinengenCollected fractions were concentrated

Vorschrift

In a 250 mL round-bottomed flask was placed 8,8′-(2-(4-nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane) (37, 246 mg, 0.581 mmol) in 2-propanol (3 mL) and dichloromethane (3 mL) to give a yellow solution. A catalytic amount of Pd on charcoal (wet) was added and the mixture was stirred under a hydrogen atmosphere for 4 hours. The mixture was filtered over Celite™, rinsed with dichloromethane and concentrated. The crude product was added to a silica gel column and was eluted with ethyl acetate in hexanes (40-60%). Collected fractions were concentrated to give the title compound (197 mg, 0.5 mmol, 86%) as a light yellow solid. For [M+H]+ mass error=0.2 mDa or 0.46 ppm.

Quelle