Sodium Sulfate → HCID 45115771, compound

HRID 1058964Notes

Reaction equation

HRID 1058964 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C@@H:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=O)[NH:11][CH2:10][C:9]1=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][N:8]1[CH2:9][CH2:10][NH:11][CH2:12][C@@H:13]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57221532HCID 57221532, compound

Product 1

HCID 45115771HCID 45115771, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

Lithium aluminium hydride (1.0M in ether, 20.2 mL, 20.2 mmol) was added to a stirred, cooled (0° C.) suspension of (6S)-1-methyl-6-(phenylmethyl)-2,5-piperazinedione (Description 34, 1.1 g, 5.0 mmol) in THF (60 mL) and the mixture was heated under reflux for 1 h. The mixture was cooled to −20° C. and saturated aqueous sodium sulfate (20.2 mL) was added. The mixture was stirred at room temperature for 15 min., filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2C2/MeOH/NH3(aq.) (90:10:1), to give the title compound as a yellow oil (0.83 g, 87%). 1H NMR (250 MHz, CDCl3) δ7.31-7.15 (5H, m), 3.17 (1H, dd, J 13.3, 3.9 Hz), 2.92-2.70 (4H, m), 2.46 (2H, m), 2.43 (3H, s), 2.27 (2H, m) and 1.51 (1H, br s). m/z (ES+) 191 (M+1).

Workup

  1. temperaturecooled
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 h
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with CH2C2/MeOH/NH3(aq.) (90:10:1)

Sources & evidence

ORD record
ord-f6a3d27642b64adc85257292a4cb49aa
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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