Reaktion #343434

Reaktionsgleichung

N-Boc-2-amino-2-methylpropanal

magnesium

2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide

magnesium

→

N-Boc-2-amino-2-methyl-4-(2,2,5,5-tetramethyl-1-cyclopentyl)butene

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto form
2. 2
   workup.DISSOLUTIONhas dissolved
3. 3
   SonstigeThe reaction is quenched with 1M HCl
4. 4
   Extraktionextracted with ether
5. 5
   Sonstigethe extracts are evaporated
6. 6
   workup.DISSOLUTIONThe residue dissolves in dioxane
7. 7
   workup.ADDITION2M H2SO4 is added
8. 8
   TemperaturThe mixture is heated until the alcohol
9. 9
   workup.ADDITIONWater is added
10. 10
    Extraktionthe mixture extracted with ether
11. 11
    TrocknenThe organic layer is dried over MgSO4
12. 12
    Sonstigeevaporated

Vorschrift

A solution of 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide in ether is added slowly to magnesium turnings until the Grignard reagent beings to form. The remainder of the alkyl bromide is then added and the mixture is stirred until all of the magnesium has dissolved. At 0° C. a solution of N-Boc-2-amino-2-methylpropanal 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 dissolves 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 extracted with ether. The organic layer is dried over MgSO4 and evaporated to give N-Boc-2-amino-2-methyl-4-(2,2,5,5-tetramethyl-1-cyclopentyl)butene.

Quelle