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

HRID 1789225Notes

Reaction equation

[CH2:1]([N:8]1[C@H:12]2[C:13](=O)[O:14][C:15](=[O:16])[C@H:11]2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C(C2C=CC=CC=2)(C)C(O)C)C=CC=CC=1.C(N(CC)CC)C.[BH4-].[Li+].[H-].Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][O:14][C:15](=[O:16])[C@H:11]2[N:10]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.673 g (2 mmol) of cis-1,3-dibenzyl-hexahydro-1H-furo[3,4-d]imidazole-2,4,6-trione and 0.435 g (2 mmol) of (-)-3,3-diphenyl-2-butanol ([α]36520 =-338.9° (1% in ethanol)) in 5 ml of toluene are heated under reflux for 6 hours in an apparatus standing under argon. After cooling 0.28 ml (2 mmol) of triethylamine and 5 ml of tetrahydrofuran are added thereto. The solution obtained is added dropwise within 30 minutes at 40° C. under argon to a solution of 4.8 ml of a 1 molar lithium borohydride solution in tetrahydrofuran (4.8 mmol) and the mixture is left to react at 40° C. for 14 hours. The excess hydride is decomposed at 10° C. with 5 ml of 3N HCl and the mixture is stirred at 60° C. for 30 minutes. The product obtained is isolated and purified as described in Example 2 and there is obtained 0.333 g of (3aS,6aR)-1,3-dibenzyl-dihydro-1H-furo[3,4-d]imidazole-2,4(3H,3aH)-dione. [α]D20 =+38.7° (1% in CHCl3), which corresponds to an optical purity of 62.4% e.e.

Workup

temperatureunder reflux for 6 hours in an apparatus
additionare added
customThe solution obtained
waitthe mixture is left
customto react at 40° C. for 14 hours
customThe product obtained
customis isolated
custompurified

Sources & evidence

ORD record: ord-a443e942722a4e3ba0857f61fd906fce
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04687859

Reaction notes

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