Tetrahydrofuran → 7,7-Difluorooctahydropyrrolo[1,2-a]pyrazine

HRID 1042889Notes

Reaction equation

HRID 1042889 reaction equation
[F:1][C:2]1([F:13])[CH2:12][N:5]2[C:6](=O)[CH2:7][NH:8][C:9](=O)[C@@H:4]2[CH2:3]1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[F:13][C:2]1([F:1])[CH2:12][N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH:4]2[CH2:3]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67316882(S)-7,7-difluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Product 1

HCID 592158907,7-Difluorooctahydropyrrolo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A pressure bottle was charged with (S)-7,7-difluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (350 mg, 1841 μmol) and THF under nitrogen, and the solution was cooled to 0° C. under nitrogen. Lithium aluminum hydride (3681 μl, 3681 μmol) was added, the mixture was allowed to warm to RT, followed by heating at reflux for 3 h. 2 mL of water was carefully added, followed by 2 mL of 6N NaOH. After stirring for 10 min, the mixture was filtered through Celite and washed with EtOAc. The filtrate was concentrated. GC/MS: [M+H]=163.

Workup

  1. temperatureto warm to RT
  2. temperatureby heating
  3. temperatureat reflux for 3 h
  4. filtrationthe mixture was filtered through Celite
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-47c52a08ac314fca8c080938588be516
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

Loading…