Diethyl Ether → N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane

HRID 1731504

Reaktionsgleichung

Reaktionsgleichung von HRID 1731504
[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH2:9]Br.[Mg].[C:13]([NH:20][C:21]1(C=O)[CH2:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[CH3:26]COCC>>[C:13]([NH:20][C:21]1([C:9]([CH:3]2[C:2]([CH3:11])([CH3:1])[CH2:6][CH2:5][C:4]2([CH3:8])[CH3:7])=[CH2:26])[CH2:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Komponenten

5

Edukt 4

HCID 3283Diethyl EtherHCID 5462224Magnesium2×HCID 10352385(1-Formylcyclopropyl)carbamic acid tert-butyl esterHCID 136292612,2,5,5-Tetramethyl-1-cyclopentylmethylbromide

Produkt 1

HCID 70445455N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane

Versuchsvorschrift

A solution of 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard reagent begins to form. The remainder of the alkyl bromide is then added and the mixture is stirred until all the magnesium dissolves. At 0° C. a solution of N-Boc-1-amino-1-cyclopropanecarboxaldehyde is then added and the mixture is stirred overnight. The reaction is quenched with 1M HCl, extracted with ether and the extracts are evaporated. The residue is dissolved in dioxane and 2M H2SO4 is added. The mixture is heated until the alcohol is dehydrated, as shown by thin layer chromatography. Water is added and the mixture is extracted with ether. The organic layer is dried over MgSO4 and evaporated to give N-Boc-1-amino-1-(2,2,5,5-tetramethyl-1-cyclopentyl)ethenylcyclopropane.

Aufarbeitung

  1. customto form
  2. dissolutiondissolves
  3. customThe reaction is quenched with 1M HCl
  4. extractionextracted with ether
  5. customthe extracts are evaporated
  6. dissolutionThe residue is dissolved in dioxane
  7. addition2M H2SO4 is added
  8. temperatureThe mixture is heated until the alcohol
  9. additionWater is added
  10. extractionthe mixture is extracted with ether
  11. dry with materialThe organic layer is dried over MgSO4
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-48aa57e5e071462eaa2c435edaaf56c7
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04622232

Verknüpfte Notizen

Wird geladen…