Réaction #215710

Équation de réaction

sodium hydroxide

lithium aluminium hydride

1-(tert.-butyloxycarbonylamino)-5-methyl-1,3-hexadiene

maleimide

→

solid

Rendement 18.7%

7-Isopropyl-4-methylamino-1,3,3a,4,7,7a-hexahydroisoindole

Rendement 18.7%

Solvants

water

water

tetrahydrofuran

ethanol

water

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 24 hours
2. 2
   TempératureAfter cooling
3. 3
   Filtrationthe solid is filtered off with suction
4. 4
   Lavagerinsed with water
5. 5
   Autreto give
6. 6
   Autreafter drying
7. 7
   Températureunder reflux for 10 hours
8. 8
   TempératureAfter cooling
9. 9
   FiltrationThe precipitate is filtered off with suction
10. 10
    Lavagerinsed with tetrahydrofuran
11. 11
    Concentrationthe combined filtrates are concentrated to dryness

Mode opératoire

50 g (0.24 mol) of 1-(tert.-butyloxycarbonylamino)-5-methyl-1,3-hexadiene are stirred together with 23 g (0.24 mol) of maleimide in 75 ml of ethanol and 75 ml of water under reflux for 24 hours. After cooling, the solid is filtered off with suction and rinsed with water to give, after drying, 56.3 g (76% of theory) of a solid of melting point 192°-195° C. 15 g (0.049 mol) are stirred together with 11 g (0.29 mol) of lithium aluminium hydride in 300 ml of tetrahydrofuran under reflux for 10 hours. After cooling, the mixture is hydrolysed with 10 ml of water, 10 ml of 10 per cent strength sodium hydroxide solution and finally 30 ml of water. The precipitate is filtered off with suction and rinsed with tetrahydrofuran and the combined filtrates are concentrated to dryness. 8.7 g of a solid are obtained and are purified by crystallisation (petroleum ether-ethyl acetate=1:5).

Source