반응 #40671

반응 방정식

TFA

tert-butyl 3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate

triethylamine

trifluroacetic anhydride

→

19a

수율 92.0%

1′-(2,2,2-trifluoroacetyl)spiro[indene-1,4′-piperidin]-3(2H)-one

수율 92.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타The reaction was evaporated
2. 2
   기타dried under high vacuum for 30 min
3. 3
   workup.DISSOLUTIONThe crude amine was dissolved in dichloromethane (25 mL)
4. 4
   세척washed with water, sat. NH4Cl solution and brine
5. 5
   건조The organics were then dried (MgSO4)
6. 6
   여과filtered
7. 7
   기타evaporated

실험 절차

TFA (25 mL) was added to a solution of commercially available tert-butyl 3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (5.0 g, 16.6 mmol) in dichloromethane (25 mL) at 0° C. The reaction was then allowed to warm to rt for 30 min. The reaction was evaporated and dried under high vacuum for 30 min. The crude amine was dissolved in dichloromethane (25 mL) and triethylamine (6.9 mL, 49.8 mmol), trifluroacetic anhydride (2.6 mL, 18.3 mmol) and DMAP (20 mg, 0.17 mmol) were added in that order. The reaction was stirred at rt for 2 h and then diluted in dichloromethane and washed with water, sat. NH4Cl solution and brine; The organics were then dried (MgSO4), filtered and evaporated to give 19a as a light yellow solid (4.55 g, 92%). (M+H)+=298. 1H NMR (400 MHz, CDCl3) δ ppm 7.75 (d, J=7.6 Hz, 1H); 7.66 (t, J=7.0 Hz, 1H); 7.48 (d, J=7.9 Hz, 1H); 7.44 (t, J=7.5 Hz, 1H); 4.69 (d,J=15.9 Hz, 1H); 4.13 (d,J=14.1 Hz, 1H); 3.30 (t,J=11.8 Hz, 1H); 2.90 (t, J=13.4 Hz, 1H); 2.68 (m, 2H); 2.05 (dt, J=13.6, 3.8 Hz, 2H); 1.66 (d, J=13.9 Hz, 2H).

출처