Benzyl Bromide → HCID 86743475, compound

HRID 1197303Notes

Reaction equation

HRID 1197303 reaction equation
[H-].[Na+].C1([C@H]([N:11]2[C@H:15]3[CH2:16][O:17][C:18](=[O:19])[C@H:14]3[NH:13][C:12]2=[O:20])C)C=CC=CC=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(COC)OC>[CH2:21]([N:13]1[CH:14]2[C:18](=[O:19])[O:17][CH2:16][CH:15]2[NH:11][C:12]1=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11075738HCID 11075738, compound

Product 1

HCID 86743475HCID 86743475, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

48 ml of dimethoxyethane and 0.39 g (16.2 mmol) of sodium hydride were placed in a 100-ml three-neck flask equipped with a magnetic stirrer under argon and with complete exclusion of moisture. Then 3.24 g (13.2 mmol) of (3aS,6aR)-1-[(R)-(1-phenylethyl)]-dihydro-1H-furo-[3,4-d]-imidazol-2,4(3H,3aH)-dione was added. After a stirring time of 10 min., 2.76 g (16.2 mmol) of benzyl bromide was added and the suspension was stirred for 30 min. Then the reaction mixture was evaporated. The residue was dissolved with 25 ml of dichloromethane and 25 ml of water. The phases were separated and the aqueous phase was washed three times, each time with 15 ml of water. The organic phases were combined, dried with 5 g of magnesium sulfate and evaporated. (3aS,6aR)-1-[R)-(1-phenylethyl)]-3-benzyl-dihydro-1H-furo-[3,4-d]-imidazol--2,4(3H,3aH)-dione was obtained as a beige product in a yield of 3.56 g (80.5 percent).

Workup

  1. customequipped with a magnetic stirrer under argon and with complete exclusion of moisture
  2. customThen the reaction mixture was evaporated
  3. dissolutionThe residue was dissolved with 25 ml of dichloromethane and 25 ml of water
  4. customThe phases were separated
  5. washthe aqueous phase was washed three times
  6. dry with materialdried with 5 g of magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-3eecb26d0c71447c9025cb6ad9602466
Source dataset
uspto-grants-1992_05
Patent number
US05117003

Reaction notes

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