Reacción #71631

Ecuación de reacción

NaHCO3

4-bromobenzaldehyde

1,1-dimethylethyl (2R,6S)-2,6-dimethyl-1-piperazinecarboxylate

sodium triacetoxyborohydride

→

title compound

Rendimiento 91.8%

1,1-Dimethylethyl (2R,6S)-4-[(4-bromophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate

Rendimiento 91.8%

Disolventes

1,2-DCE

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture stirred for 30 mins
2. 2
   ExtracciónThe product was extracted into EtOAc
3. 3
   Secadothe extracts dried (Na2SO4)
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in DCM
6. 6
   workup.ADDITIONtreated with PS-hydrazine resin
7. 7
   workup.STIRRINGwith stirring for 2 h
8. 8
   OtroThe resin was removed by filtration
9. 9
   Otrothe solvent removed in vacuo

Procedimiento

A mixture of 4-bromobenzaldehyde (1.85 g, 10 mmol), 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-1-piperazinecarboxylate (2.15 g, 10 mmol) and sodium triacetoxyborohydride (3.18 g) in 1,2-DCE (35 ml) was stirred at room temperature for 3 days. Saturated aq. NaHCO3 solution was added and the mixture stirred for 30 mins. The product was extracted into EtOAc and the extracts dried (Na2SO4) and concentrated. The residue was dissolved in DCM and treated with PS-hydrazine resin with stirring for 2 h. The resin was removed by filtration and the solvent removed in vacuo. Chromatography (0-40% EtOAc/hexane) gave the title compound (3.52 g). MS (ES): MH+ 383/385.

Fuente