Reacción #160089

Ecuación de reacción

tert-butyl 4-(aminomethyl)-4-hydroxy-piperidine-1-carboxylate

ethyl 2-bromo-2,2-difluoro-acetate

→

tert-butyl 4-[[(2-bromo-2,2-difluoro-acetyl)amino]methyl]-4-hydroxy-piperidine-1-carboxylate

Rendimiento 99.2%

Disolventes

N,N-dimethylformamide

ethyl acetate

water

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe organic layer was dried over Na2SO4
2. 2
   Filtraciónfiltered
3. 3
   Concentraciónconcentrated

Procedimiento

To a solution of tert-butyl 4-(aminomethyl)-4-hydroxy-piperidine-1-carboxylate (3.00 g, 13.0 mmol) in N,N-dimethylformamide (30 mL) was added ethyl 2-bromo-2,2-difluoro-acetate (2.65 g, 13.0 mmol) and the reaction mixture stirred for 1 h under nitrogen. The reaction mixture was mixture diluted with ethyl acetate and water (25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated to provide tert-butyl 4-[[(2-bromo-2,2-difluoro-acetyl)amino]methyl]-4-hydroxy-piperidine-1-carboxylate (4.98 g, 12.9 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ 9.04 (t, J=5.9 Hz, 1H), 4.66 (s, 1H), 3.65 (d, J=12.7 Hz, 2H), 3.16 (d, J=6.1 Hz, 2H), 3.02 (s, 2H), 1.38 (m, 13H).

Fuente