反応 #78257

反応方程式

sodium hydride

4-bromobenzyl bromide

(2S,4R)-N-Boc-4-hydroxy-2-methyl-proline methyl ester

→

(2S,4R)-N-Boc-4-(4-bromo-benzyloxy)-2-methyl-proline

収率 28.4%

溶媒

water

THF

THF

THF

反応条件

後処理

1. 1
   温度The reaction mixture was refluxed for 3 h
2. 2
   抽出extracted with EtOAc
3. 3
   抽出extracted with DCM
4. 4
   洗浄The combined organic extracts were washed with water
5. 5
   乾燥dried over MgSO4
6. 6
   その他evaporated under reduced pressure

実験手順

To a suspension of sodium hydride (60% in oil) (0.12 g) (1.5 eq.) in 5 mL of dry THF was added (2S,4R)-N-Boc-4-hydroxy-2-methyl-proline methyl ester (0.55 g) in 5 mL of dry THF. The reaction mixture was stirred for 45 min., and a solution of 4-bromobenzyl bromide (0.75 g) (1.5 eq.) in 5 mL of dry THF was added. The reaction mixture was refluxed for 3 h. After cooling to RT, the reaction mixture was diluted with water and extracted with EtOAc. The aqueous layer was acidified and extracted with DCM. The combined organic extracts were washed with water, dried over MgSO4 and evaporated under reduced pressure to afford (2S,4R)-N-Boc-4-(4-bromo-benzyloxy)-2-methyl-proline (0.25 g).

出典