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

HRID 2413396Notes

Reaction equation

HRID 2413396 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@H:14]([C:15](OC)=[O:16])[C@H:13]([C:19](O)=[O:20])[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]1=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[Ca+2].[Cl-].Cl>C(O)C>[CH2:22]([N:12]1[C@H:13]2[CH2:19][O:20][C:15](=[O:16])[C@H:14]2[N:10]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:11]1=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 11428617(4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

Product 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dioneYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a mixture of sodium borohydride (0.55 g) and 99.5% ethanol (20 ml) were added dropwise a solution of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]365b =-27.7 ° at c=1 in DMF, 2.00 g) in 99.5% ethanol (30 ml) at 0°-5° C. and a solution of anhydrous calcium chloride (0.80 g) in 99.5% ethanol (8 ml) at the same temperature. The obtained mixture was allowed to warm up to room temperature and to react at the same temperature for 18 hours under stirring. Then, 1N hydrochloric acid was added dropwise to the reaction mixture. The solvent was removed from the mixture at 50°-55° C. under reduced pressure. The residue was shaken with chloroform (50 ml) and water (50 ml). Chloroform layer was washed successively with 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was treated with ether (10 ml), filtered and dried to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (1.43 g). M.P., 116°-117° C. [α]D25 =+60.9° (c=1, CHCl3).

Workup

  1. customto react at the same temperature for 18 hours
  2. customThe solvent was removed from the mixture at 50°-55° C. under reduced pressure
  3. stirringThe residue was shaken with chloroform (50 ml) and water (50 ml)
  4. washChloroform layer was washed successively with 5% aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with ether (10 ml)
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-ca7e8d6d4a0a4082a49625806e836231
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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