Tetrabutylammonium Fluoride → Tert-butyl 4-(2-hydroxyethyl)-3-oxopiperazine-1-carboxylate

HRID 2105883Notes

Reaction equation

HRID 2105883 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[C:10](=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68638537Tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 68874055Tert-butyl 4-(2-hydroxyethyl)-3-oxopiperazine-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-tert-butyloxycarbonyl-1-[2-(tert-butyldimethylsilyloxy)ethyl]-piperazin-2-one (0.88 g, 2.5 mmol) in tetrahydrofuran (30 mL) was added tetrabutylammonium fluoride (3.6 mL, 3.6 mmol, 1.0 M in tetrahydrofuran) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with a dilute aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The organic extracts were washed with brine and dried over anhydrous sodium sulfate. Purification of the crude residue by flash column chromatography (silica gel, eluting with 30% ethyl acetate in hexanes) gave 4-tert-butyloxycarbonyl-1-(2-hydroxyethyl)-piperazin-2-one (0.45 g, 75%).

Workup

  1. customThe reaction mixture was quenched with a dilute aqueous solution of sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customPurification of the crude residue
  6. washby flash column chromatography (silica gel, eluting with 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e120db236f6c4cd7a0e74b7cba032dd5
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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