반응 #10277

반응 방정식

4-bromobutyraldehyde dimethyl acetal

sodium hydride

5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

→

4-(4,4-dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

수율 51.8%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타the solvent was removed
2. 2
   기타the residue was partitioned between water and ethyl acetate
3. 3
   세척The organic phase was washed with water
4. 4
   건조dried (magnesium sulfate)
5. 5
   농축concentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in diethyl ether
7. 7
   여과the suspension was filtered
8. 8
   농축the filtrate was concentrated
9. 9
   기타Purification by silica gel chromatography
10. 10
    세척eluting with 2% methanol in chloroform

실험 절차

To a suspension of 60% sodium hydride in mineral oil (0.2 g, 5 mmole) in N,N-dimethylformamide (6 mL) was added 5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.0 g, 4.67 mmole). The reaction mixture was warmed at 50° C. for 5 minutes, and then at room temperature for 15 minutes. To the resulting solution was added 4-bromobutyraldehyde dimethyl acetal (0.99 g, 5 mmole). After the reaction mixture was stirred at room temperature for 16 hours, the solvent was removed, and the residue was partitioned between water and ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate), and concentrated. The residue was dissolved in diethyl ether, and the suspension was filtered, and the filtrate was concentrated. Purification by silica gel chromatography, eluting with 2% methanol in chloroform, gave 4-(4,4-dimethoxybutyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.8 g,) as a heavy syrup. Nmr: (chloroform-d) δ (ppm) 1.49, s, (9H); 2.64, m, 3H; 3.32, s (3H); 4.37, m, (1H).

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