تفاعل #614918

معادلة التفاعل

(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid

EDC

3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol

(R)-1,2,3,4-tetrahydronaphthalen-1-amine

DIEA

→

title compound

المردود 83.0%

(R)-tert-Butyl 3,3-dimethyl-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,3-azasilolidine-1-carboxylate

المردود 83.0%

المذيبات

DMF

DMF

ethyl acetate

brine

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at rt for 1.5 h
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried over MgSO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was purified by flash column chromatography on SiO2 (eluting with 20% EtOAc/hexane)

الإجراء التجريبي

To a solution of (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid (1.0 g, 3.9 mmol) in DMF (9 mL) at 0° C. was added EDC (1.3 g, 6.6 mmol) and 3H-[1,2,3]-triazolo[4,5-b]pyridin-3-ol (0.53 g, 3.9 mmol). The resulting mixture was stirred for 5 minutes and treated with a solution of (R)-1,2,3,4-tetrahydronaphthalen-1-amine (Alfa Aesar, 0.60 g, 4.1 mmol) in DMF (4 mL) and then DIEA (0.94 mL, 5.4 mmol). The reaction mixture was stirred at rt for 1.5 h and diluted with ethyl acetate and brine. The organic layer was separated, washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on SiO2 (eluting with 20% EtOAc/hexane) to afford the title compound (1.25 g, 83%). 1H NMR (400 MHz, CDCl3) δ 7.22-7.02 (m, 4H), 5.22-4.61 (m, 2H), 3.16-2.65 (m, 3H), 2.52 (d, J=14.5 Hz, 1H), 2.12-1.95 (m, 1H), 1.88-1.76 (m, 3H), 1.52-1.28 (m, 11H), 0.43-0.16 (m, 6H); MS(ESI+) m/z 389.4 (M+H)+.

المصدر