تفاعل #426598

معادلة التفاعل

furan-3-carboxylic acid

HOBt

EDCI.HCl

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

→

(R)—N-(1,2,3,4-tetrahydronaphthalen-1-yl)-2,5-dihydrofuran-3-carboxamide

المذيبات

CH2Cl2

DMF

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   غسيلThe resulting solution was washed with saturated NaHCO3, H2O, brine
2. 2
   تجفيفdried over MgSO4
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىRecrystallization from EtOH/H2O

الإجراء التجريبي

To a solution of furan-3-carboxylic acid (100 mg, 0.68 mmol), HOBt (240 mg, 1.78 mmol) and EDCI.HCl (196 mg, 1.03 mmol) in CH2Cl2 (8 mL) and DMF (1.5 mL) at 0° C., was added (R)-1,2,3,4-tetrahydronaphthalen-1-amine (160 μL, 1.06 mmol). The reaction was stirred at rt for 24 h, after which CH2Cl2 was added. The resulting solution was washed with saturated NaHCO3, H2O, brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from EtOH/H2O afforded (R)—N-(1,2,3,4-tetrahydronaphthalen-1-yl)-2,5-dihydrofuran-3-carboxamide. 1H NMR (500 MHz, CDCl3): δ 1.89 (m, 3H), 2.12 (m, 1H), 2.84 (m, 2H), 5.35 (m, 1H), 5.96 (br d, 1H, J=7.75 Hz), 6.59 (dd, 1H, J=1.90, 0.86 Hz), 7.13 (m, 1H), 7.19 (m, 2H), 7.32 (m, 1H), 7.43 (t, 1H, J=1.73 Hz), 7.93 (m, 1H). MS (M+H, 242).

المصدر