Reacción #50044

Ecuación de reacción

compound

N-Cbz-L-proline

dimethyl sulfide

→

title product

Rendimiento 98.0%

N-Cbz-L-prolinol

Rendimiento 98.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to 0° C.
2. 2
   Otroquenched by careful addition of 10% acetic acid in methanol
3. 3
   OtroThe mixture was reduced in volume on a rotary evaporator
4. 4
   workup.DISSOLUTIONthe concentrate was dissolved in ethyl acetate
5. 5
   Lavadowhich was washed successively with 1N HCl, water and sodium bicarbonate solution
6. 6
   ExtracciónThe organic extract
7. 7
   Secadowas dried over Na2SO4
8. 8
   Concentraciónconcentrated

Procedimiento

A 21.56 g (86.55 mmol) sample of the compound from step 24a above was dissolved in 200 mL of THF, and the solution was cooled to 0° C. BH3 -dimethyl sulfide (86.5 mL, 2N) was added dropwise under a nitrogen atmosphere. The reaction was stirred at room temperature for 16 hr, then cooled to 0° C. and quenched by careful addition of 10% acetic acid in methanol. The mixture was reduced in volume on a rotary evaporator, and the concentrate was dissolved in ethyl acetate, which was washed successively with 1N HCl, water and sodium bicarbonate solution. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 19.94 g (98% yield).

Fuente