Cyclo(-Gly-Phe) → (S)-2-Benzylpiperazine

HRID 897385Notes

Reaction equation

HRID 897385 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:14]1[C:19](=O)[NH:18][CH2:17][C:16](=O)[NH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([C@H:14]1[CH2:19][NH:18][CH2:17][CH2:16][NH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7076549Cyclo(-Gly-Phe)HCID 21226445Aluminium lithium hydride

Product 1

HCID 20760001(S)-2-Benzylpiperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.6 g, 42.16 mmol) was added in portions to a stirred mixture of (S)-2-benzyl piperazine-3,6-dione (3.0 g, 14.70 mmol) and tetrahydrofuran (80 ml) at 0° C. After 30 min at ice-bath temperature, the mixture was refluxed for 4 h with stirring. The reaction was quenched by the portionwise addition of sodium sulfate decahydrate and some methanol until hydrogen evolution ceased. It was filtered and the solids were washed several times with dichloromethane. The combined filtrates were evaporated to leave a white solid.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe reaction was quenched by the portionwise addition of sodium sulfate decahydrate
  3. filtrationIt was filtered
  4. washthe solids were washed several times with dichloromethane
  5. customThe combined filtrates were evaporated
  6. customto leave a white solid

Sources & evidence

ORD record
ord-1f9be3ee8b754e5a9c6af48b8bc34050
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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