Реакция #7736

Уравнение реакции

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

Растворители

DMF

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGto stir at room temperature until the reaction
2. 2
   Другоеis complete by TLC, approximately 12 hours
3. 3
   ДругоеThe reaction solution is partitioned between ethyl acetate and water
4. 4
   Экстракцияthe water layer being extracted several times more with solvent
5. 5
   ДругоеThe combined organic layers are dried
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

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.

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