Ethanol → 4-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylate

HRID 2300808Notes

Reaction equation

HRID 2300808 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24](OC)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+].C(O)C>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH:12]1[CH2:24][OH:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 44519651-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

Product 1

HCID 235310394-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylateYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.32 g of methyl 1-(benzyloxycarbonyl)-4-(tert-butyloxycarbonyl)piperazine-2-carboxylate in 30 mL of THF was added 834 mg of lithium chloride, 744 mg of sodium borohydride, and 30 mL of ethanol. The mixture was stirred overnight at room temperature, concentrated, and redissolved in 200 mL of CH2Cl2. This CH2Cl2 solution was washed with 100 mL of water and 100 mL of brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 2:1 hexanes-EtOAc to 1:1 hexanes-EtOAc, to yield 2.65 g of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in 200 mL of CH2Cl2
  3. washThis CH2Cl2 solution was washed with 100 mL of water and 100 mL of brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with a gradient system of 2:1 hexanes-EtOAc to 1:1 hexanes-EtOAc

Sources & evidence

ORD record
ord-d317efaa5e7b4411b9ab5f42e535b857
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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