Tetrahydrofuran → HCID 59427319, compound

HRID 1042885Notes

Reaction equation

HRID 1042885 reaction equation
[F:1][C@H:2]1[CH2:12][N:5]2[C:6](=O)[CH2:7][NH:8][C:9](=O)[CH:4]2[CH2:3]1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[F:1][C@H:2]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 67316924HCID 67316924, compound

Product 1

HCID 59427319HCID 59427319, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A pressure bottle was charged with (7R)-7-fluoro-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (200 mg, 1162 μmol) and 4.6 mL THF, and the bottle was purged with nitrogen and cooled to 0° C. Lithium aluminum hydride (2323 μl, 2323 μmol) was added. The mixture was allowed to warm to RT, and was then heated at reflux for 4 h. The reaction was cooled to 0° C. and 1 mL water was added carefully, followed by 1 mL 6N NaOH. The mixture was stirred for 15 min, and was filtered through a pad of Celite, washing with EtOAc. The filtrate was concentrated and a sample was analyzed by H-NMR and GC/MS: [M+H]=145.

Workup

  1. customthe bottle was purged with nitrogen
  2. temperatureto warm to RT
  3. temperaturewas then heated
  4. temperatureat reflux for 4 h
  5. temperatureThe reaction was cooled to 0° C.
  6. filtrationwas filtered through a pad of Celite
  7. washwashing with EtOAc
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-59fe87e5144f4c9396d4cb0006c4eb8a
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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