반응 #78257

반응 방정식

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

수율 28.4%

용매

water

THF

THF

THF

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 3 h
2. 2
   추출extracted with EtOAc
3. 3
   추출extracted with DCM
4. 4
   세척The combined organic extracts were washed with water
5. 5
   건조dried over MgSO4
6. 6
   기타evaporated under reduced pressure

실험 절차

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).

출처