Réaction #40671

Équation de réaction

TFA

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

triethylamine

trifluroacetic anhydride

→

19a

Rendement 92.0%

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

Rendement 92.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was evaporated
2. 2
   Autredried under high vacuum for 30 min
3. 3
   workup.DISSOLUTIONThe crude amine was dissolved in dichloromethane (25 mL)
4. 4
   Lavagewashed with water, sat. NH4Cl solution and brine
5. 5
   SéchageThe organics were then dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated

Mode opératoire

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).

Source