1,2-DIHYDRO-2-OXO-SPIRO[3H-INDOLE-3,4'-PIPERIDINE]-1'-CARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER Chemical Properties

Boiling point:

475.6±45.0 °C(Predicted)

Density 

1.22±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C

pka

13.83±0.20(Predicted)

form 

powder

color 

Yellow

Safety Information

HS Code 

2933998090

1,2-DIHYDRO-2-OXO-SPIRO[3H-INDOLE-3,4'-PIPERIDINE]-1'-CARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER Usage And Synthesis

Synthesis

Spiro[indoline-3,4'-piperidin]-2-one (2.73 g, 11.42 mmol) and di-tert-butyl dicarbonate (2.74 g, 12.57 mmol) were used as the raw materials. Spiro[indoline-3,4'-piperidin]-2-one was dissolved in tetrahydrofuran (100 mL), and then di-tert-butyl dicarbonate and triethylamine (2.38 mL, 17.135 mmol) were added in turn at room temperature. 17.135 mmol). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was treated with a mixture of water and dichloromethane. The aqueous layer was extracted three times with dichloromethane, the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give tert-butyl 2-oxospiro[dihydroindole-3,4'-piperidine]-1'-carboxylate (4.02 g, quantitative yield) as a white foam. The product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 1.44 (s, 9H), 1.56-1.73 (m, 4H), 3.55-3.79 (m, 4H), 6.86 (dd, J = 7.70, 0.40 Hz, 1H), 6.95 (td, J = 7.59, 1.10 Hz, 1H), 7.19 (td , J = 7.70, 1.10 Hz, 1H), 7.43 (dd, J = 6.80, 0.70 Hz, 1H), 10.41 (br.s., 1H); m/z = 303.05 (M + H).

References

[1] Patent: WO2014/60411, 2014, A1. Location in patent: Page/Page column 36; 37

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