Trifluoroacetic acid → (rac)-(3aRS, 6aSR)-1-Ethyl-hexahydro-cyclopentaimidazol-2-one

HRID 1497349Notes

Reaction equation

HRID 1497349 reaction equation
C(OC([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10]([CH2:16][CH3:17])[C:9]1=[O:18])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:16]([N:10]1[CH:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[NH:8][C:9]1=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123307876(rac)-(3aSR,6aRS)-3-Ethyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 123776686(rac)-(3aRS, 6aSR)-1-Ethyl-hexahydro-cyclopentaimidazol-2-oneYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3aSR,6aRS)-3-methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 1, step 2) (1.60 g, 6.29 mmol) in 15 ml of dichloromethane was added trifluoroacetic acid (5.74 g, 3.9 ml, 50.3 mmol, 8 equiv.) and the yellow solution was stirred for 15 h at room temperature. The reaction mixture was quenched by addition of saturated sodium bicarbonate solution and the pH of the aqueous phase was set to 9. After workup with dichloromethane/water, the organic phases were dried, filtered and concentrated in vaccuo to yield 0.801 g of a yellow oil, which directly used in the next step without further characterization.

Workup

  1. customThe reaction mixture was quenched by addition of saturated sodium bicarbonate solution
  2. dry with materialAfter workup with dichloromethane/water, the organic phases were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-92d36cca20b34870858711084f1964c4
Source dataset
uspto-grants-2015_12
Patent number
US09199971B2

Reaction notes

Loading…