Trifluoroacetic acid → (3aRS,6aSR)-1-Methyl-hexahydro-cyclopentaimidazol-2-one
Reaction equation
C(O[C:6]([N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[N:10](C)[C:9]1=[O:17])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:6][N:8]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[NH:10][C:9]1=[O:17]Participants
Procedure
To a solution of (3aSR,6aRS)-3-methyl-2-oxo-hexahydro-cyclopentaimidazole-1-carboxylic acid tert-butyl ester (Example 106, step 2) (1.99 g, 8.28 mmol) in 30 ml of dichloromethane was added trifluoroacetic acid (7.55 g, 5.1 ml, 66.3 mmol, 8 equiv.) and the yellow solution was stirred at for 5 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 vacuo to yield 1.07 g of an off-white solid, which was taken up in cold ethyl acetate and filtered to yield the title compound (822 mg, 71%) as a crystalline white solid which was directly used in the next step without further characterisation.
Workup
- customThe reaction mixture was quenched by addition of saturated sodium bicarbonate solution
- dry with materialAfter workup with dichloromethane/water, the organic phases were dried
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f060c4495d64438386ce2300eba6dc33
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513273B2
Reaction notes
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