Hydrochloric Acid → (3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

HRID 1463109Notes

Reaction equation

HRID 1463109 reaction equation
[CH2:1]([N:8]1[C@@H:12]([C:13](Cl)=O)[C@@H:11]([C:16]([O:18]C2CCCCC2)=[O:17])[N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl>O1CCCC1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:17][C:16](=[O:18])[C@H:11]2[N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 56625349HCID 56625349, compound

Product 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

45.5 g (100 mmol) of cyclohexyl (4S,5R)-1,3-dibenzyl-5-chlorocarbonyl-2-oxo-4-imidazolidinecarboxylate (prepared according to Example 1) are dissolved in 50 ml of tetrahydrofuran. To the clear solution are added dropwise at 0° C. within 60 minutes 80 ml of a 1M lithium borohydride solution in tetrahydrofuran (80 mmol). The mixture is then stirred at 0° C. for a further 30 minutes. 100 ml of 1N hydrochloric acid are then cautiously added dropwise at 0° C. The mixture is then stirred at 70° C. for 30 minutes and subsequently concentrated in a rotary evaporator to 100 ml. Thereto there are added 200 ml of water and the mixture is left to crystallize at 0° C. for 18 hours. The crystallized-out crude product is filtered off under suction and washed neutral with water. After drying at 60° C. in vacuo for 4 hours, the crude product is dissolved in 100 ml of hot isopropanol and then left to crystallize at 0° C. for 18 hours. The product is then filtered off under suction and rinsed twice with 20 ml of ice-cold isopropanol each time. After drying at 60° C. in a water-jet vacuum for 6 hours, there are obtained 26.5 g of (3aS,6aR)-1,3-dibenzyldihydro-1H-furo[3,4-d]imidazole-2,4(3H,3aH)-dione with a melting point of 116°-117° C.

Workup

  1. stirringThe mixture is then stirred at 70° C. for 30 minutes
  2. concentrationsubsequently concentrated in a rotary evaporator to 100 ml
  3. additionThereto there are added 200 ml of water
  4. waitthe mixture is left
  5. customto crystallize at 0° C. for 18 hours
  6. customThe crystallized-out crude product
  7. filtrationis filtered off under suction
  8. washwashed neutral with water
  9. customAfter drying at 60° C. in vacuo for 4 hours
  10. dissolutionthe crude product is dissolved in 100 ml of hot isopropanol
  11. waitleft
  12. customto crystallize at 0° C. for 18 hours
  13. filtrationThe product is then filtered off under suction
  14. washrinsed twice with 20 ml of ice-cold isopropanol each time
  15. dry with materialAfter drying at 60° C. in a water-jet vacuum for 6 hours

Sources & evidence

ORD record
ord-f0a3ecf7fea2414392702e37ca145183
Source dataset
uspto-grants-1984_07
Patent number
US04463180

Reaction notes

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