3-Chloro-2-chloromethyl-1-propene → Benzyl tert-butyl 4-methylidenepyrazolidine-1,2-dicarboxylate

HRID 7640

Reaktionsgleichung

Reaktionsgleichung von HRID 7640
[H-].[Na+].[C:3]([NH:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl[CH2:23][C:24]([CH2:26]Cl)=[CH2:25]>CN(C=O)C>[C:18]([O:17][C:15]([N:14]1[CH2:26][C:24](=[CH2:23])[CH2:25][N:13]1[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 24758Sodium hydrideHCID 11288582Benzyl tert-butyl hydrazine-1,2-dicarboxylate

Produkt 1

HCID 12970152Benzyl tert-butyl 4-methylidenepyrazolidine-1,2-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringto stir at room temperature until the reaction
  2. customis complete by TLC, approximately 12 hours
  3. customThe reaction solution is partitioned between ethyl acetate and water
  4. extractionthe water layer being extracted several times more with solvent
  5. customThe combined organic layers are dried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-16ce0de6403640198e3f969730ca292f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087615B2

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