Water → HCID 86680329, compound

HRID 2279178Notes

Reaction equation

HRID 2279178 reaction equation
[CH2:1]([C@H:3]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7](=O)[C@H:6]([CH3:19])[NH:5][C:4]1=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>C1COCC1>[CH2:1]([C@@H:3]1[CH2:4][NH:5][C@@H:6]([CH3:19])[CH2:7][N:8]1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86680331HCID 86680331, compound

Product 1

HCID 86680329HCID 86680329, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (3S,6R)-6-ethyl-1-(4-methoxy-benzyl)-3-methyl-piperazine-2,5-dione (5.34 g) in 130 ml of THF was added 160 ml of a 1 M solution of lithium aluminium hydride in THF. The mixture was stirred overnight and then heated to reflux for 4 h. At 0° C. 5 ml of water, followed by 16 ml of 1 M aqueous KOH-solution were added. The resulting suspension was stirred for 30 min at r.t. and filtered by suction over Celite. The filtrate was concentrated in vacuo and freeze-dried. 3.68 g (77%) of the title compound were obtained and used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customAt 0° C
  4. additionwere added
  5. stirringThe resulting suspension was stirred for 30 min at r.t.
  6. filtrationfiltered by suction over Celite
  7. concentrationThe filtrate was concentrated in vacuo
  8. customfreeze-dried

Sources & evidence

ORD record
ord-46e8460b161a4899a58c5c7a009fe318
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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