反応 #78417

反応方程式

Boc-trans-4-hydroxy-L-proline methyl ester

Imidazole

tert-butyldimethylsilyl chloride

→

desired product 1

収率 120.9%

trans-4-Hydroxy-Cbz-L-Proline

収率 120.9%

溶媒

DMF

反応条件

後処理

1. 1
   その他DMF was removed via vacuum rotary evaporation
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   洗浄The solution was washed with 1M HCl and brine
4. 4
   乾燥The organic solution was dried over MgSO4
5. 5
   濃縮concentrated
6. 6
   その他The crude product was purified by column chromatography
7. 7
   洗浄eluting with hexanes/ethyl acetate (4/1

実験手順

Boc-trans-4-hydroxy-L-proline methyl ester (10.35 g, 0.04 mol) was dissolved in DMF (135 mL). Imidazole (13.6 g, 0.20 mol) was added, followed by the addition of tert-butyldimethylsilyl chloride (18.1 g, 0.12 mol) and the solution was stirred overnight at room temperature. DMF was removed via vacuum rotary evaporation and the residue was dissolved in ethyl acetate. The solution was washed with 1M HCl and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (4/1, v/v) to afford 12.83 g (89% yield) of the desired product 1 as a colorless oil.

出典