Reacción #167108

Ecuación de reacción

4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

2,6-di-tert-butyl-4-methylpyridine

iodomethane

→

title compound

Rendimiento 53.0%

4-Methoxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Rendimiento 53.0%

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónwas filtered over elite
2. 2
   ConcentraciónThe filtrate was concentrated to a residue which
3. 3
   workup.DISSOLUTIONwas dissolved in diethyl ether
4. 4
   LavadoThe organic solution was washed with 10% HCl and brine
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex)

Procedimiento

4-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (861 mg, 3.32 mmol) was dissolved in DCM (6.6 mL) then 2,6-di-tert-butyl-4-methylpyridine (1.023 g, 4.98 mmol) and AgOTf (938 mg, 3.65 mmol) were added. The reaction mixture was cooled to 0° C. and iodomethane (0.25 mL, 3.98 mmol) was added. After 4 min, the reaction mixture was diluted with DCM and it was filtered over elite. The filtrate was concentrated to a residue which was dissolved in diethyl ether. The organic solution was washed with 10% HCl and brine, then dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 80% EtOAc/Hex) to afford the title compound (479 mg, 53%).

Fuente