تفاعل #75946

معادلة التفاعل

carbamate

benzyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methylcarbamate

triethylamine

t-butyl acrylate

→

product

المردود 95.0%

tert-butyl (2E)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]-2-propenoate

المردود 95.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىpreviously degassed with argon for 20 minutes
2. 2
   درجة الحرارةThe resulting mixture was heated
3. 3
   درجة الحرارةat gentle reflux for 26 hours
4. 4
   أخرىThe catalyst was removed by filtration
5. 5
   تركيزThe filtrate was concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (50 mL)
7. 7
   غسيلwashed with water (50 mL), brine (50 mL)
8. 8
   تجفيفdried over anhydrous sodium sulfate
9. 9
   ترشيحfiltered over a pad of silica gel
10. 10
    أخرىRemoval of solvent in vacuo

الإجراء التجريبي

Palladium acetate (224 mg, 1 mmol) was added to a mixture of the carbamate of Example 11 (4.2 g, 10 mmol), triethylamine (2.1 mL, 15 mmol), and t-butyl acrylate (1.76 mL, 12 mmol) in acetonitrile (50 mL) previously degassed with argon for 20 minutes. The resulting mixture was heated at gentle reflux for 26 hours. It was cooled to room temperature. The catalyst was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate, and filtered over a pad of silica gel. Removal of solvent in vacuo afforded the product as an oil (4.0 g, 95%): 1H NMR (CDCl3) δ1.50 (s, 9H), 1.70 1.85 (m, 1H), 200 (m, 1H), 2.80 (m, 2H), 3.40(m, 1H), 3.65 (m, 1H), 5.12 (s, 2H), 5.25 (m, 1H), 6.21 (d, J=15.3 Hz,1H), 6.76 (d, J=8.4 Hz, 1H), 7.20-7.40 (m, 7H), 7.49 (d, J=15.9 Hz, 1H); CI-MS m/z 424 (M+H+).

المصدر