Réaction #45038

Équation de réaction

Methyl 4-iodobenzoate

tert-butyl 1,4-diazepane-1-carboxylate

caesium carbonate

2-acetylcyclohexanone

→

tert-butyl 4-(4-methoxycarbonylphenyl)-1,4-diazepane-1-carboxylate

Rendement 13.2%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONdissolved in DCM (50 ml)
3. 3
   Lavagewashed with water (20 ml), saturated ammonium chloride solution (20 ml)
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated
7. 7
   AutreThe crude product was purified by silica column chromatography
8. 8
   Lavageeluting with 0-1% MeOH in DCM
9. 9
   workup.ADDITIONThe product containing fractions
10. 10
    Autreevaporated
11. 11
    Autredried in vacuo

Mode opératoire

Methyl 4-iodobenzoate (1.00 g, 3.82 mmol, 1.0 eq) was dissolved in DMF and tert-butyl 1,4-diazepane-1-carboxylate (765 mg, 3.82 mmol, 1.0 eq), caesium carbonate (2.49 g, 7.63 mmol, 2.0 eq), 2-acetylcyclohexanone (101 μl, 0.76 mmol, 0.20 eq [20 mol %]) and copper iodide (37 mg, 0.19 mmol, 0.05 eq [5 mol %]) were added. The reaction mixture was stirred at 90° C. under nitrogen for 7 h. The reaction mixture was evaporated, dissolved in DCM (50 ml), washed with water (20 ml), saturated ammonium chloride solution (20 ml), dried over MgSO4, filtered and evaporated. The crude product was purified by silica column chromatography, eluting with 0-1% MeOH in DCM. The product containing fractions were combined, evaporated and dried in vacuo to give tert-butyl 4-(4-methoxycarbonylphenyl)-1,4-diazepane-1-carboxylate (168 mg, 13%) as a yellow oil.

Source