Reaktion #89054

Reaktionsgleichung

NaBH4

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

NaBH4

→

tert-butyl (1-benzyl-5-fluoro-1,2,3,4-tetrahydropyridin-2-yl)methylcarbamate

Ausbeute 62.0%

Lösungsmittel

MeOH

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred for extra 40 min
2. 2
   Waschenwashed with brine
3. 3
   SonstigeEtOAc layer was separated
4. 4
   Trocknendried with MgSO4
5. 5
   Einengenconcentrated in vacuo

Vorschrift

NaBH4 (5.56 mmol, 0.21 g) was added to a solution of 1-benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide (1.40 mmol, 0.60 g) in MeOH at 0° C. The resulting mixture was stirred at 0° C. for 40 min. An aliquot was checked by analytical HPLC and some of the starting material remained. Additional NaBH4 (5.56 mmol, 0.21 g) was added at 0° C. and the resulting mixture was stirred for extra 40 min. The reaction mixture was diluted with EtOAc and washed with brine. EtOAc layer was separated, dried with MgSO4 and concentrated in vacuo to give desired tert-butyl (1-benzyl-5-fluoro-1,2,3,4-tetrahydropyridin-2-yl)methylcarbamate in 62% yield which was used for next step without further purification. MS (ESI) 321 (M+H).

Quelle