تفاعل #40671

معادلة التفاعل

TFA

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

triethylamine

trifluroacetic anhydride

→

19a

المردود 92.0%

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

المردود 92.0%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was evaporated
2. 2
   أخرىdried under high vacuum for 30 min
3. 3
   workup.DISSOLUTIONThe crude amine was dissolved in dichloromethane (25 mL)
4. 4
   غسيلwashed with water, sat. NH4Cl solution and brine
5. 5
   تجفيفThe organics were then dried (MgSO4)
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated

الإجراء التجريبي

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).

المصدر