反応 #7736

反応方程式

NaH

N-Cbz-N′-Boc-hydrazine

3-chloro-2-chloromethyl-propene

→

desired product

4-methylenepyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGto stir at room temperature until the reaction
2. 2
   その他is complete by TLC, approximately 12 hours
3. 3
   その他The reaction solution is partitioned between ethyl acetate and water
4. 4
   抽出the water layer being extracted several times more with solvent
5. 5
   その他The combined organic layers are dried
6. 6
   ろ過filtered
7. 7
   濃縮concentrated

実験手順

To a suspension of NaH (3.81 g, 95.4 mmol) in DMF (80 mL) is add dropwise a solution of N-Cbz-N′-Boc-hydrazine (12.1 g, 45.4 mmol) in DMF (20 mL). The reaction mixture is stirred about 20 minutes and 3-chloro-2-chloromethyl-propene (5.8 mL, 50 mmol) is added dropwise and the reaction is allowed to stir at room temperature until the reaction is complete by TLC, approximately 12 hours. The reaction solution is partitioned between ethyl acetate and water, the water layer being extracted several times more with solvent. The combined organic layers are dried, filtered, and concentrated to afford the desired product as a clear oil which is used without further purification.

出典