반응 #593050

반응 방정식

1,3-oxazolidine-2,4-dione

1,1,3,3-tetramethylguanidine

1,1-dimethylethyl 4-{[(methylsulphonyl)oxy]methyl}piperidine-1-carboxylate

→

1,1-dimethylethyl 4-[(2,4-dioxo-1,3-oxazolidin-3-yl)methyl]piperidine-1-carboxylate

용매

tetrahydrofuran

dimethylformamide

반응 조건

후처리

1. 1
   기타prepared in step 2.1
2. 2
   온도is heated
3. 3
   온도at reflux for 24 hours
4. 4
   기타to return to ambient temperature
5. 5
   농축is concentrated under reduced pressure
6. 6
   기타water and the aqueous phase is separated off
7. 7
   추출extracted twice with dichloromethane
8. 8
   세척The combined organic phases are washed with saturated aqueous sodium chloride solution
9. 9
   건조dried over sodium sulphate
10. 10
    기타evaporation of the solvent
11. 11
    기타the residue obtained
12. 12
    기타is purified by chromatography on silica gel
13. 13
    세척eluting with a 98/2
14. 14
    workup.ADDITION95/5 mixture of dichloromethane and methanol

실험 절차

A suspension of 13.60 g (46.36 mmol) of 1,1-dimethylethyl 4-{[(methylsulphonyl)oxy]methyl}piperidine-1-carboxylate, prepared in step 2.1., 9.37 g (92.72 mmol) of 1,3-oxazolidine-2,4-dione and 16.02 g (139.08 mmol) of 1,1,3,3-tetramethylguanidine in a mixture of 180 ml of tetrahydrofuran and 30 ml of dimethylformamide is heated at reflux for 24 hours. It is allowed to return to ambient temperature and is concentrated under reduced pressure. The residue is taken up in dichloromethane and water and the aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Following evaporation of the solvent, the residue obtained is purified by chromatography on silica gel, eluting with a 98/2 then 95/5 mixture of dichloromethane and methanol.

출처