반응 #338186

반응 방정식

4-aminobutyraldehyde dimethyl acetal

1,1′-carbonyldiimidazole

DIPEA

benzyloxyamine hydrochloride

→

3-(4,4-dimethoxy-butyl)-1-(benzyloxy)-urea

수율 74.1%

용매

THF

반응 조건

후처리

1. 1
   농축The mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONthe residue was dissolved in DMF (50 mL)
3. 3
   농축then concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (200 mL)
5. 5
   세척the solution was washed with brine (5×25 mL)
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated
8. 8
   기타Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc followed by 100% EtOAc)

실험 절차

To a solution of 4-aminobutyraldehyde dimethyl acetal (2.73 g, 20.5 mmol) in THF (50 mL) was added 1,1′-carbonyldiimidazole (3.39 g, 20.9 mmol) and the resultant mixture was stirred at room temperature for 45 minutes. The mixture was concentrated under reduced pressure and the residue was dissolved in DMF (50 mL) and treated with DIPEA (18 mL, 103 mmol) and benzyloxyamine hydrochloride (10.2 g, 64.0 mmol). The mixture was heated at 60° C. overnight then concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and the solution was washed with brine (5×25 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc followed by 100% EtOAc) provided 4.29 g (73%) of 3-(4,4-dimethoxy-butyl)-1-(benzyloxy)-urea as a yellow oil.

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