Piperidine → 2-Methyl-2-(1-thiocarbamoylpiperidin-4-yl)propionic acid ethyl ester

To a solution of 9-fluorenylmethoxycarbonylisothiocyanate (2.62 g, 9.32 mmol) in chloroform (20 ml), a solution of 2-methyl-2-piperidin-4-yl-propionic acid ethyl ester hydrochloride (2.27 g, 9.61 mmol) in chloroform (10 ml) and sodium hydrogen carbonate (4.03 g, 48.0 mmol) were added and the mixture was stirred at room temperature. Further, piperidine (30 ml) was added and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated in vacuo, and the solid obtained by adding diethyl ether was collected by filtration. The solid was dissolved in N,N-dimethylformamide (20 ml) and piperidine (20 ml) was added and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over sodium sulfate, and the residue obtained by vacuum concentration was purified by silica gel chromatography (n-hexane:ethyl acetate) and the title compound (2.4 g, 98%) was obtained.

1. stirringthe mixture was stirred at room temperature for 2 hours
2. concentrationThe reaction solution was concentrated in vacuo
3. customthe solid obtained
4. filtrationwas collected by filtration
5. dissolutionThe solid was dissolved in N,N-dimethylformamide (20 ml)
6. additionpiperidine (20 ml) was added
7. stirringthe mixture was stirred at room temperature for 1 hour
8. additionWater was added to the reaction solution
9. extractionthe solution was extracted with ethyl acetate
10. washThe organic layer was washed with a saturated brine
11. dry with materialdried over sodium sulfate
12. customthe residue obtained by vacuum concentration
13. customwas purified by silica gel chromatography (n-hexane:ethyl acetate)

ORDレコード

ord-e67f054afcdd49e98fe7eca1b6a64c5e

出典データセット

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07803801B2