Sodium Hydroxide → HCID 59454321, compound

HRID 1914768Notes

Reaction equation

HRID 1914768 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[NH:15][C:14](=O)[CH2:13][N:12]([CH3:17])[C:11]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>[CH2:1]([O:8][CH2:9][C@H:10]1[NH:15][CH2:14][CH2:13][N:12]([CH3:17])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59454389HCID 59454389, compound

Product 1

HCID 59454321HCID 59454321, compoundYield 83.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 21226445Aluminium lithium hydrideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-3-Benzyloxymethyl-1-methyl-piperazine-2,5-dione (1.93 g, 7.78 mmol) in THF (30 mL), LiAlH4 1M in THF (15 mL, 15.5 mmol) was added dropwise over 30 min and the solution was refluxed under N2 atmosphere for 3 h. The reaction was cooled to 0° C. and diluted with water (100 mL). Then 4 mL of a 15% aqueous NaOH solution was added. After 1 h 100 mL of water was added and the reaction stirred overnight. The white precipitate was filtered out and washed with DCM. The solvent was removed under reduced pressure and the residue was diluted with Et2O and decanted. The crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol, 90:9:1) to give the desired compound (1.43 g, 83.5% yield) as yellow oil.

Workup

  1. temperaturethe solution was refluxed under N2 atmosphere for 3 h
  2. filtrationThe white precipitate was filtered out
  3. washwashed with DCM
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was diluted with Et2O
  6. customdecanted
  7. customThe crude was purified by flash chromatography (DCM/MeOH/7N NH3 in methanol, 90:9:1)

Sources & evidence

ORD record
ord-fda8162fd4124398bc63e16adbbe34ac
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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