Trifluoroacetic acid → Hexahydrocyclopenta(c)pyrrol-5(1H)-one

HRID 1925073Notes

Reaction equation

HRID 1925073 reaction equation
C(OC([N:8]1[CH2:12][CH:11]2[CH2:13][C:14](=[O:16])[CH2:15][CH:10]2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:9]1[CH:10]2[CH2:15][C:14](=[O:16])[CH2:13][CH:11]2[CH2:12][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10998690tert-Butyl 5-oxohexahydrocyclopenta(c)pyrrole-2(1H)-carboxylate

Product 1

HCID 46911901Hexahydrocyclopenta(c)pyrrol-5(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reacting starting material 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester (I-1a) with trifluoroacetic acid in the solvent of dichloromethane in an ice-water bath to obtain hexahydro-cyclopenta[c]pyrrol-5-one triflutate (I-1b); reacting hexahydro-cyclopenta[c]pyrrol-5-one triflutate (I-1b) with acyl chloride or ester in the presence of base to give the compounds of formula (I-1c); reacting the compounds of formula (I-1c) with equivalent amounts of different amines, sodium triacetoxyborohydride and triethylamine in the solvent of methanol at room temperature to obtain the compounds of formula (IB).

Sources & evidence

ORD record
ord-b962ce8d55fc468fb5b4942c154dda61
Source dataset
uspto-grants-2012_05
Patent number
US08178575B2

Reaction notes

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