tert-Butoxy bis(dimethylamino)methane → 1-Tert-butyl 3-ethyl 5-((dimethylamino)methylene)-4-oxopiperidine-1,3-dicarboxylate

HRID 505631

Reaktionsgleichung

Reaktionsgleichung von HRID 505631
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(O[CH:25](N(C)C)[N:26]([CH3:28])[CH3:27])(C)C>C1(C)C=CC=CC=1>[CH3:25][N:26]([CH:28]=[C:7]1[CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1=[O:1])[CH3:27]

Komponenten

4

Edukt 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Produkt 1

HCID 684658601-Tert-butyl 3-ethyl 5-((dimethylamino)methylene)-4-oxopiperidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2b (272 mg, 1.00 mmol) in dry toluene (4.0 mL) was added Bredereck's reagent (183 mg, 1.05 mmol) dropwise over 2 minutes. The mixture stirred at rt for 1 h and heated to 60° C. for 24 h. The mixture was concentrated and the residue purified on a SiO2 column (CH2Cl2, 50% EtOAc-hexanes then EtOAc for elution) to give a viscous oil. The oil was dissolved in 50% Et2O-hexanes and concentrated to give the title compound 3b as a waxy white solid; 243 mg, 74%. This material was used immediately without further purification.

Aufarbeitung

  1. temperatureheated to 60° C. for 24 h
  2. concentrationThe mixture was concentrated
  3. customthe residue purified on a SiO2 column (CH2Cl2, 50% EtOAc-hexanes
  4. washEtOAc for elution)
  5. customto give a viscous oil
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d2a4d8a3dc9349719342c7abedc32bd7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781474B2

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