Hydrochloric Acid → (3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione

HRID 463738Notes

Reaction equation

HRID 463738 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13](OC)=[O:14])[C@H:11]([C:17](O)=[O:18])[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C1(C)C=CC=CC=1.C(O)(C)C>[CH2:20]([N:10]1[C@@H:11]2[CH2:17][O:18][C:13](=[O:14])[C@@H:12]2[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

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

Product 1

HCID 11427250(3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dioneYield 93.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent

Procedure

A solution of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =+27.7° at c=1.0 in DMF, 368 mg) in toluene (2 ml) and isopropanol (3 ml) was added dropwise to a suspension of sodium borohydride (100 mg) in toluene at 5°-10° C. The obtained mixture was allowed to warm up to room temperature and to react at the same temperature for 18 hours. Then, 1N hydrochloric acid (10 ml) was added dropwise to the mixture. The mixture was stirred at 55°-60° C. for 30 minutes. Aqueous layer was separated from organic layer and extracted once with toluene (15 ml). The organic layers were combined, washed successively with water, 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated to give (3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (301 mg). M.P., 116°-118° C. [α]D25 =-61.8° (c=1, CHCl3).

Workup

  1. customto react at the same temperature for 18 hours
  2. customAqueous layer was separated from organic layer
  3. extractionextracted once with toluene (15 ml)
  4. washwashed successively with water, 5% aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7132a57822484d77bc4744d10d522e3f
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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