Triphenylphosphine → (S)-1-benzyl-3-ethylpiperazine-2-one

HRID 249874Notes

Reaction equation

HRID 249874 reaction equation
[NH2:1][C@@H:2]([CH2:16][CH3:17])[C:3]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7]O)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:9]([N:5]1[CH2:6][CH2:7][NH:1][C@@H:2]([CH2:16][CH3:17])[C:3]1=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 66874126(S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide

Product 1

HCID 45095306(S)-1-benzyl-3-ethylpiperazine-2-oneYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazidodicarboxylate (1.82 g, 9.3 mmol) was added to solution of (S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide (1.84 g, 7.8 mmol) and triphenylphosphine (2.62 g, 10.0 mmol) in THF (50 mL). The reaction mixture was stirred at room temperature for 7 d. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 10% CH3OH in EtOAc) to afford (S)-1-benzyl-3-ethylpiperazine-2-one (0.8 g, 47%) as clear oil. 1H NMR consistent.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, 10% CH3OH in EtOAc)

Sources & evidence

ORD record
ord-729d3d4d430a4bb685c6c1aadc70cc45
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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