반응 #45038

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Methyl 4-iodobenzoate

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

caesium carbonate

2-acetylcyclohexanone

→

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

수율 13.2%

용매

DMF

반응 조건

후처리

1. 1
   기타The reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONdissolved in DCM (50 ml)
3. 3
   세척washed with water (20 ml), saturated ammonium chloride solution (20 ml)
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The crude product was purified by silica column chromatography
8. 8
   세척eluting with 0-1% MeOH in DCM
9. 9
   workup.ADDITIONThe product containing fractions
10. 10
    기타evaporated
11. 11
    기타dried in vacuo

실험 절차

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.

출처