반응 #50044

반응 방정식

compound

N-Cbz-L-proline

dimethyl sulfide

→

title product

수율 98.0%

N-Cbz-L-prolinol

수율 98.0%

용매

THF

반응 조건

후처리

1. 1
   온도cooled to 0° C.
2. 2
   기타quenched by careful addition of 10% acetic acid in methanol
3. 3
   기타The mixture was reduced in volume on a rotary evaporator
4. 4
   workup.DISSOLUTIONthe concentrate was dissolved in ethyl acetate
5. 5
   세척which was washed successively with 1N HCl, water and sodium bicarbonate solution
6. 6
   추출The organic extract
7. 7
   건조was dried over Na2SO4
8. 8
   농축concentrated

실험 절차

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).

출처