Reacción #86290

Ecuación de reacción

(5-amino-1,3-phenylene)dimethanol

2-(methyldithio)isobutyraldehyde

sodium borohydride

→

(5-(2-methyl-2-(methyldisulfanyl)propylamino)-1,3-phenylene)dimethanol

Rendimiento 65.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISSOLUTIONuntil completely dissolved (3 hours)
2. 2
   Otrowas then quenched slowly with cold 5% HCl solution
3. 3
   workup.ADDITIONThe mixture was diluted with dichloromethane
4. 4
   Extracciónthen extracted with dichloromethane
5. 5
   Lavadowashed with brine
6. 6
   SecadoThe organic extracts were dried over anhydrous sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroPurification by silica gel chromatography (MeOH/DCM)

Procedimiento

(5-amino-1,3-phenylene)dimethanol (2.5 g, 16.32 mmol) and 2-(methyldithio)isobutyraldehyde (2.347 ml, 16.32 mmol) were stirred at ambient temperature in absolute ethanol (82 ml) until completely dissolved (3 hours). The mixture was cooled to 0° C. in an ice bath and sodium borohydride (0.741 g, 19.59 mmol) was added. The reaction was stirred for 1 hour at 0° C., and was then quenched slowly with cold 5% HCl solution. The mixture was diluted with dichloromethane and the pH was adjusted to pH=8 with saturated sodium bicarbonate solution then extracted with dichloromethane and then washed with brine. The organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (MeOH/DCM) yielded (5-(2-methyl-2-(methyldisulfanyl)propylamino)-1,3-phenylene)dimethanol (3g, 65%) as a white solid. 1H NMR (400 Hz, CDCl3): δ6.62 (s, 1H), 6.54 (s, 2H), 4.53 (s, 4H), 3.13 (s, 2H), 2.30 (s, 3H), 1.32 (s, 6H). See FIG. 47.

Fuente