Iodoethane → (rac)-(3aSR,6aRS)-3-Ethyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

HRID 1497348Notes

Reaction equation

HRID 1497348 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[NH:10][C:9]1=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:20][CH3:21]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10]([CH2:20][CH3:21])[C:9]1=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67437675(3aSR, 6aRS)-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 123307876(rac)-(3aSR,6aRS)-3-Ethyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl esterYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3aSR,6aRS)-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 1, step 1) (1.50 g, 6.63 mmol) in 25 ml of DMF was added a 60% suspension of sodium hydride in mineral oil (207 mg, 8.62 mmol, 1.3 equiv.). The suspension was stirred for 45 minutes at room temperature (gas evolution), then iodoethane (1.34 g, 0.696 ml, 8.62 mmol, 1.3 equiv.) was added and the mixture was stirred at room temperature overnight. After concentration in vaccuo and workup with ethyl acetate/water, 1.60 g of a yellow oil were obtained containing mineral-oil drops which was directly used in the next step without further characterization.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationAfter concentration in vaccuo and workup with ethyl acetate/water

Sources & evidence

ORD record
ord-7d4d9e39799c4cd88e58d75b4b364982
Source dataset
uspto-grants-2015_12
Patent number
US09199971B2

Reaction notes

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