Dimethylformamide → Tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate

HRID 1809560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809560
[OH:1][N:2]=[CH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.CN(C=O)C.[Cl:22]N1C(=O)CCC1=O>[Cl-].[Na+].O>[Cl:22][C:3](=[N:2][OH:1])[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 72698249Tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate

Produkt 1

HCID 76573117Tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A 250 mL flask was charged with tert-butyl 4-((hydroxyimino)methyl)piperidine-1-carboxylate (2.0 g, 8.8 mmol) and DMF (100 mL). 1-chloropyrrolidine-2,5-dione (1.2 g, 8.8 mmol) was added and stirred at ambient temperature overnight. The reaction was poured into 1:1 brine:water and extracted with EtOAc. The organic layer was washed twice with water, dried over sodium sulfate, filtered and concentrated to afford tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate (2.3 g, 100%).

Aufarbeitung

  1. extractionwater and extracted with EtOAc
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e30fc72fc48a4cea800efdb408739fa7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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