Reacción #1884031

Ecuación de reacción

N-(tert-butoxycarbonyl)-D-methionine

sodium bis(2-methoxyethoxy)aluminum hydride

Rochelle salt

→

desired product

Rendimiento 76.9%

tert-butyl (1R)-1-(hydroxymethyl)-3-(methylsulfanyl)propylcarbamate

Rendimiento 76.9%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with diethyl ether
2. 2
   LavadoThe extract was washed sequentially with brine and aqueous NaHCO3
3. 3
   Secadodried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated

Procedimiento

A solution of N-(tert-butoxycarbonyl)-D-methionine (12.47 g, 50 mmol) and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al®) (50 mmol) in dry toluene (125 mL) was stirred at 0° C. for 30 minutes, then at ambient temperature for 1 hour. The mixture was treated with aqueous Rochelle salt and extracted with diethyl ether. The extract was washed sequentially with brine and aqueous NaHCO3, dried (MgSO4), filtered, and concentrated to provide the desired product (9.05 g).

Fuente