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

HRID 2413398Notes

Reaction equation

HRID 2413398 reaction equation
ClC(OCC)=O.[CH2:7]([N:14]1[C@H:18]([C:19](OC)=[O:20])[C@H:17]([C:23](O)=[O:24])[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH2:26]([N:16]1[C@H:17]2[CH2:23][O:24][C:19](=[O:20])[C@H:18]2[N:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]1=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 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 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl chloroformate (0.54 g) in tetrahydrofuran (2 ml) was added dropwise to a mixture of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =-27.4° at c=1 in DMF, 1.84 g), triethylamine (0.51 g) and tetrahydrofuran (10 ml) at -5° C. The mixture was stirred at the same temperature for 30 minutes. Precipitated triethylamine hydrochloride was filtered off and the filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90 % aqueous tetrahydrofuran (10 ml) at -15° C. After reacting, the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was concentrated under reduced pressure and the residue was purified by chromatography on silica gel column to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (1.04 g). M.P., 114°-117° C. [α]D20 =+59.0° (c=1, CHCl3).

Workup

  1. filtrationPrecipitated triethylamine hydrochloride was filtered off
  2. additionthe filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90 % aqueous tetrahydrofuran (10 ml) at -15° C
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel column

Sources & evidence

ORD record
ord-1bdb33f3dec54cca964ccc5c8552c0bc
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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