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To a solution of spiroindole (3.32 mmol, 1.07 g) in DMF (5 mL) at 0C, NaH (4.98 mmol, 119 mg) added and stirred for 10 min. Then to the mixture boc- anhydride (4.31 mmol, 942 mg) was added and stirred for 4 hr. The reaction mixture diluted with water (50 mL), extracted with ethylacetate (2 x 50 mL), the ethylacetate layer was washed with brine, dried over Na2S04, evaporated under reduced pressure and the crude was purified by flash column chromatography. |
587.3 mg |
With dimethylaminopyridine; In chloroform; at 20℃; for 1h; |
The 1?-benzyloxycarbonylspiro[indoline-3,4?-piperidine] (487.0 mg) was dissolved in chloroform (15 mL), ditert-butyl dicarbonate (0.416 mL) and dimethylaminopyridine (221.5 mg) were added thereto, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried with anhydrous magnesium sulfate and was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 25/75) to obtain the title compound (587.3 mg). 1H-NMR (400MHz,CDCl3) delta: 1.58(br.s,9H),1.77-1.88(m,2H),2.90-3.03(m,2H),3.80-3.93(m,2 H),4.16-4.29(m,2H),5.17(s,2H),6.95-6.99(m,1H),7.06-7.09(m,1 H),7.16-7.22(m,1H),7.30-7.96(m,6H). MS (ESI)m/z:423[M+H]+. |