Water → HCID 54474705, compound

HRID 1038558Notes

Reaction equation

HRID 1038558 reaction equation
[CH2:1]([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][CH2:10][C@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C.[C:20]([O:24][C:25](=O)[O:26]C(C)(C)C)([CH3:23])([CH3:22])[CH3:21].O>O1CCCC1>[CH2:1]([N:8]1[C@@H:9]([CH3:15])[CH2:10][N:11]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[C@H:12]([CH3:14])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1146TrimethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 10632028(2R,5S)-1-benzyl-2,5-dimethylpiperazine

Product 1

HCID 54474705HCID 54474705, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,5S)-1-benzyl-2,5-dimethylpiperazine (3.52 g, 17.2 mmol) in tetrahydrofuran (50 mL), trimethylamine (2.12 g, 20.9 mmol) and di-tert-butylcarbonate (4.56 g, 20.9 mmol) were added under ice-cold conditions, and the mixture was stirred for 15 minutes. Then, the mixture was stirred at room temperature for 5.5 hours. The reaction solution was added water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (3.16 g, 60%) was obtained as a pale yellow oil.

Workup

  1. stirringThen, the mixture was stirred at room temperature for 5.5 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fbe5005b02a4492ab1f8a3ec964f245f
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…