Trifluoroacetic acid → Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate

HRID 1961570Notes

Reaction equation

HRID 1961570 reaction equation
[O:1]=[C:2]1[CH2:16][CH:5]2[CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8][CH:4]2[CH2:3]1.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[CH2:6]1[CH:5]2[CH2:16][C:2](=[O:1])[CH2:3][CH:4]2[CH2:8][NH:7]1

Participants

4

Reactant 2

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

Product 1

HCID 68625929Hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 5-oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylate 1e (0.32 g, 1.42 mmol) was dissolved in 10 mL of dichloromethane with stirring. Upon cooling by an ice-water bath, trifluoroacetic acid (3.27 mL, 42.7 mmol) was added and the reaction mixture was reacted for 30 minutes at 0° C. The mixture was concentrated under reduced pressure to obtain the crude title compound hexahydro-cyclopenta[c]pyrrol-5-one trifluoroacetate 1f, which was directly used in the next step.

Workup

  1. temperatureUpon cooling by an ice-water bath
  2. customthe reaction mixture was reacted for 30 minutes at 0° C
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fd24d459e67b47158971acd137be31c5
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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