Réaction #3757

Équation de réaction

isobutyl chloroformate

N-methylmorpholine

trans-2-phenyl-cyclopentanecarboxylic acid

1,3-diallyl-5,6-diaminouracil

→

trans-2-phenyl-cyclo-pentanecarboxylic acid

3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enylamide

Rendement 87.8%

Solvants

tetrahydrofuran

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   TempératureCool
3. 3
   Autrethe reaction to -20° C.
4. 4
   Autrethe reaction for 30 minutes
5. 5
   workup.STIRRINGstir at -20° C. for 3 hours
6. 6
   workup.ADDITIONdilute
7. 7
   AutreSeparate the layers
8. 8
   Lavagerinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml)
9. 9
   Séchagedry over anhydrous magnesium sulfate
10. 10
    Filtrationfilter
11. 11
    Concentrationconcentrate under vacuum
12. 12
    AutrePurify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate)

Mode opératoire

Dissolve trans-2-phenyl-cyclopentanecarboxylic acid (1.0 g, 5.3 mmol), prepared according to F. G. Bordwell and J. Almy, J. Org. Chem., 38, 571 (1973), in tetrahydrofuran (20 ml) and add N-methylmorpholine (0.58 ml, 5.3 mmol). Cool the reaction to -20° C. and add isobutyl chloroformate (0.69 ml, 5.3 mmol). Stir the reaction for 30 minutes, add 1,3-diallyl-5,6-diaminouracil (1.2 g, 5.3 mmol, in 4 ml dimethylformamide) and stir at -20° C. for 3 hours. Warm to room temperature and dilute the reaction with diethyl ether (400 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate) to provide trans-2-phenyl-cyclo-pentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enylamide (0.51 g).

Source