反応 #50044

反応方程式

compound

N-Cbz-L-proline

dimethyl sulfide

→

title product

収率 98.0%

N-Cbz-L-prolinol

収率 98.0%

溶媒

THF

反応条件

後処理

1. 1
   温度cooled to 0° C.
2. 2
   その他quenched by careful addition of 10% acetic acid in methanol
3. 3
   その他The mixture was reduced in volume on a rotary evaporator
4. 4
   workup.DISSOLUTIONthe concentrate was dissolved in ethyl acetate
5. 5
   洗浄which was washed successively with 1N HCl, water and sodium bicarbonate solution
6. 6
   抽出The organic extract
7. 7
   乾燥was dried over Na2SO4
8. 8
   濃縮concentrated

実験手順

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).

出典