反応 #78246

反応方程式

L-proline

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

sodium hydride

4-bromobenzyl bromide

→

trans-N-Boc-4-(4-bromo-benzyloxy)-L-proline

収率 30.6%

溶媒

water

THF

THF

THF

反応条件

後処理

1. 1
   その他was prepared
2. 2
   温度The reaction mixture was refluxed for 3 hours
3. 3
   抽出extracted with EtOAc
4. 4
   抽出extracted with DCM
5. 5
   洗浄The combined organic extracts were washed with water
6. 6
   乾燥dried over MgSO4
7. 7
   その他evaporated under reduced pressure

実験手順

The compound of formula (P5), wherein R′ is 4-Bromo and the bonds linking the benzyloxy and methyl ester groups (depicted in P5 as wavy bonds) define the trans, L-proline configuration (2S,4R) was prepared as follows. To a suspension of sodium hydride (60% in oil) (0.12 g) (1.5 eq.) in 5 mL of dry THF was added trans-N-Boc-4-hydroxy-L-proline methyl ester (0.5 g) in 5 mL of dry THF. The reaction mixture was stirred for 45 minutes 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 hours. 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 trans-N-Boc-4-(4-bromo-benzyloxy)-L-proline (0.25 g). NMR (CDCl3, 200 MHz): 7.47 (2H, d), 7.2 (2H, d), 4.50-4.30 (3H, m), 4.25-4.1 (1H, m), 3.75 (3H, s), 3.8-3.5 (2H, m), 2.5-2.3 (1H, m), 2.15-1.95 (1H, m), 1.5-1.35 (9H).

出典