Reaktion #50944

Reaktionsgleichung

NaH

N-Cbz-N′-Boc-hydrazine

3-chloro-2chloromethyl-propene

→

desired product

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

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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-2chloromethyl-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.

Quelle