Reacción #307055

Ecuación de reacción

tert-butyllithium

1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine

dry ice

→

title compound

3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)benzoic acid

Disolventes

Et2O

Et2O EtOAc

water

Et2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Secadodried over MgSO4
2. 2
   Otrothe solvents were removed under reduced pressure
3. 3
   Otroto give a yellow oil that
4. 4
   Otrowas triturated in iPr2O (˜20 mL)
5. 5
   Filtraciónpentane (˜20 mL), filtered off
6. 6
   Lavadowashed with pentane

Procedimiento

To anhydrous Et2O (130 mL) at −78° C. was added tert-butyllithium (63.79 mL; 1.50 M; 95.68 mmol) (solution in pentane) which was followed by the slow addition of a solution of 1-[4-bromo-2-(methoxymethyl)phenyl]-2-methylpiperidine (12.97 g; 43.49 mmol) in anhydrous Et2O (20 mL). After 40 min, the reaction mixture was poured on an excess of freshly crushed dry ice and stirred for 30 min after which time it was diluted with Et2O/EtOAc (1:1, 800 mL), water (200 mL, pH 4-5). The organic layers were combined, dried over MgSO4 and the solvents were removed under reduced pressure to give a yellow oil that was triturated in iPr2O (˜20 mL) and pentane (˜20 mL), filtered off and washed with pentane to give the title compound as a beige powder. LC/MS (Method B): 264.1 (M+H)+.

Fuente