HCID 10857710, compound → HCID 11075738, compound

HRID 373397Notes

Reaction equation

HRID 373397 reaction equation
[C:1]1([C@H:7]([N:9]2[C:13]3[CH2:14][O:15][C:16](=[O:17])[C:12]=3[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN(C)C=O.[Rh]>[C:1]1([C@H:7]([N:9]2[C@H:13]3[CH2:14][O:15][C:16](=[O:17])[C@H:12]3[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 10857710HCID 10857710, compound

Product 1

HCID 11075738HCID 11075738, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 8.98 g (36.8 mmol) of 1-[(R)-(1-phenylethyl)]-1H-furo-[3,4-d]-imidazol-2,4(3H,6H)-dione in 90 ml of dimethylformamide was placed in a 250-ml autoclave and 0.90 g of Rh/Al2O3 (5 percent) is added. Then the autoclave was flushed twice successively with hydrogen, and filled to 40 bars. The mixture was stirred for 10 hours. Then the catalyst was filtered off. The solvent was evaporated at 13.3 mbar and the residue was recrystallized with 10 ml of ethyl acetate. (3aS,6aR)-1-[(R)-(1-phenylethyl)]-dihydro-1H-furo-[3,4-d]-imidazol-2,4(3H,3aH)-dione was obtained as a white crystalline product in a yield of 4.89 g=54 percent. Concerning the product:

Workup

  1. additionis added
  2. customThen the autoclave was flushed twice successively with hydrogen
  3. additionfilled to 40 bars
  4. filtrationThen the catalyst was filtered off
  5. customThe solvent was evaporated at 13.3 mbar
  6. customthe residue was recrystallized with 10 ml of ethyl acetate

Sources & evidence

ORD record
ord-632a5521ab7f426fbe44d408454d89aa
Source dataset
uspto-grants-1992_11
Patent number
US05162540

Reaction notes

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