Reaktion #89053

Reaktionsgleichung

benzyl bromide

benzyl bromide

tert-butyl (5-fluoropyridin-2-yl)methylcarbamate

→

1-benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   Waschenwas rinsed with ether until benzyl bromide
3. 3
   WaschenThen, the silica pad was rinsed with MeOH
4. 4
   SonstigeRemoval of MeOH in vacuo

Vorschrift

A mixture of benzyl bromide (4.21 mmol, 0.5 mL), tert-butyl (5-fluoropyridin-2-yl)methylcarbamate (3.49 mmol, 0.79 g) and acetone (4 mL) in a sealed tube was heated to 80° C. overnight. According to analytical HPLC, around 50% of the starting material remained. Additional benzyl bromide (33.68 mmol, 4.0 mL) was added and the reaction was continued for extra 8 h. The reaction mixture was concentrated in vacuo and loaded on a pad of silica which was rinsed with ether until benzyl bromide was gone. Then, the silica pad was rinsed with MeOH. Removal of MeOH in vacuo afforded desired product 1-benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide as light orange solid in 43% yield. MS (ESI) 317 (M+H).

Quelle