Trifluoroacetic acid → (S)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

HRID 421182Notes

Reaction equation

HRID 421182 reaction equation
ClC[C:3]([NH:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](OC(C)(C)C)=O)=[O:4].C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:6]1[NH:5][C:3](=[O:4])[CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:7]12

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 59215816(S)-tert-Butyl 2-((2-chloroacetamido)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 59215765(S)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

1,1-Dimethylethyl (2S)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate (D11; 1.24, 4.5 mmol), was dissolved in 20 ml of DCM and treated with TFA (5 ml) at room temperature. After 1 h complete conversion into the desired material was observed and the reaction mixture was loaded onto a SCX cartridge. The product obtained after elution with 2M NH3 in MeOH was then dissolved in acetonitrile (30 ml) and treated with sodium carbonate (1.43 g, 10.34 mmol). The reaction mixture was heated at 60° C. for 6 hours; the crude obtained after removal is purified by flash-chromatography eluting with dichloromethane/MeOH 95/5 affording 310 mg.

Workup

  1. customThe product obtained
  2. washafter elution with 2M NH3 in MeOH
  3. dissolutionwas then dissolved in acetonitrile (30 ml)
  4. customthe crude obtained
  5. customafter removal
  6. customis purified by flash-chromatography
  7. washeluting with dichloromethane/MeOH 95/5 affording 310 mg

Sources & evidence

ORD record
ord-3a368cd391954a4d9431dcf9339a95cf
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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