Reaktion #162767

Reaktionsgleichung

n-Butyllithium

Intermediate 12a

1-(3-Bromo-benzyl)-4,4-difluoro-piperidine

di-tert-butyl azodicarboxylate

→

title compound

Ausbeute 43.2%

Di-tert-butyl 1-{3-[(4,4-difluoropiperidin-1-yl)methyl]phenyl}hydrazine-1,2-dicarboxylate

Ausbeute 43.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at −78° C. for 20 min
2. 2
   Temperaturto warm to RT over 20 min
3. 3
   SonstigeThe mixture was then partitioned between saturated ammonium chloride solution (15 mL) and ethyl acetate (3×20 mL)
4. 4
   WaschenThe combined organic extracts were washed with brine (20 mL)
5. 5
   Trocknendried (Na2SO4)
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigethe residue purified by FCC
8. 8
   Wascheneluting with 0-100% EtOAc in pentane

Vorschrift

n-Butyllithium (1.6 M in hexanes, 4.5 mL, 7.28 mmol) was added dropwise to a stirred solution of Intermediate 12a (1.98 g, 6.82 mmol) in dry THF (15 mL) at −78° C. under nitrogen. The mixture was stirred at −78° C. for 10 min, then di-tert-butyl azodicarboxylate (1.73 g, 7.51 mmol) was added in one portion. The mixture was stirred at −78° C. for 20 min, then allowed to warm to RT over 20 min. The mixture was then partitioned between saturated ammonium chloride solution (15 mL) and ethyl acetate (3×20 mL). The combined organic extracts were washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and the residue purified by FCC, eluting with 0-100% EtOAc in pentane, to give the title compound as a pale yellow oil (1.30 g, 43%). LCMS (Method 1): Rt 2.54 min, m/z 442 [MH+].

Quelle