反応 #593050

反応方程式

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

溶媒

tetrahydrofuran

dimethylformamide

反応条件

後処理

1. 1
   その他prepared in step 2.1
2. 2
   温度is heated
3. 3
   温度at reflux for 24 hours
4. 4
   その他to return to ambient temperature
5. 5
   濃縮is concentrated under reduced pressure
6. 6
   その他water and the aqueous phase is separated off
7. 7
   抽出extracted twice with dichloromethane
8. 8
   洗浄The combined organic phases are washed with saturated aqueous sodium chloride solution
9. 9
   乾燥dried over sodium sulphate
10. 10
    その他evaporation of the solvent
11. 11
    その他the residue obtained
12. 12
    その他is purified by chromatography on silica gel
13. 13
    洗浄eluting with a 98/2
14. 14
    workup.ADDITION95/5 mixture of dichloromethane and methanol

実験手順

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.

出典