(R)-3-Methyl-2-(pyrazin-2-yl)butan-2-ol → (2R)-3-methyl-2-(piperazin-2-yl)butan-2-ol

HRID 1046582Notes

Reaction equation

HRID 1046582 reaction equation
[CH3:1][CH:2]([CH3:12])[C@:3]([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)([OH:5])[CH3:4].[H][H]>[Pt]=O.CO>[CH3:1][CH:2]([CH3:12])[C@:3]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)([OH:5])[CH3:4]

Participants

5

Reactant 2

HCID 66797466(R)-3-Methyl-2-(pyrazin-2-yl)butan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 66797442(2R)-3-methyl-2-(piperazin-2-yl)butan-2-olYield 93.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Platinum oxide (4.673 g, 20.58 mmol) was placed in a Parr bottle. Methanol (140 mL) was added under an atmosphere of nitrogen followed by (R)-(+)-3-methyl-2-(pyrazin-2-yl)butan-2-ol (17.1 g, 102.9 mmol). The reaction mixture was shaken in a PARR hydrogenator overnight with a hydrogen pressure of 60 psi. Lc/Ms after this time indicate that the reaction was complete. The suspension was filtered through a pad of celite under a nitrogen atmosphere, rinsing with methanol. The crude mixture was concentrated in vacuo. The residue was re-dissolved in dichloromethane, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as viscous light yellow oil (16.6 g, 93%); 1H NMR (CDCl3) 0.82-1.08 (9H, m), 1.81 (1H, m), 2.20-3.17 (10H, m); MS ES(+) 173.0 (M+1).

Workup

  1. filtrationThe suspension was filtered through a pad of celite under a nitrogen atmosphere
  2. washrinsing with methanol
  3. concentrationThe crude mixture was concentrated in vacuo
  4. dissolutionThe residue was re-dissolved in dichloromethane
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95e1dd0617764ec3bea50a1bfad37839
Source dataset
uspto-grants-2013_10
Patent number
US08569337B2

Reaction notes

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