1-Piperazinecarboxylic acid, ethyl ester → HCID 69795127, compound

HRID 895336Notes

Reaction equation

HRID 895336 reaction equation
[C:1]1([C@@H:7]2[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][C:13]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14])[CH3:11]>C(O)C>[CH2:10]([O:12][C:13]([N:15]1[CH2:16][CH2:17][N:18]([C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][OH:8])[CH2:19][CH2:20]1)=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 114705(+)-Styrene oxide

Product 1

HCID 69795127HCID 69795127, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round-bottomed flask fitted with a reflux condenser and a thermometer, 15 g (125 mmoles) of (R)-phenyloxirane, 19.75 g (125 mmoles, 18.3 ml) of ethyl-N-piperazine carboxylate, and 80 ml of ethyl alcohol were introduced. The mixture was heated at reflux for 3 hours. Volatile substances were removed under reduced pressure and the resulting mixture was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/aqueous ammonia 98.5/1.5/0.5 (v/v/v)), affording 8.8 g of (S)-4-(2-Hydroxy-1-phenyl-ethyl)-piperazine-1-carboxylic acid ethyl ester (compound 2) as a colorless oil. Yield: 25%.

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 hours
  4. customVolatile substances were removed under reduced pressure
  5. customthe resulting mixture was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/aqueous ammonia 98.5/1.5/0.5 (v/v/v))

Sources & evidence

ORD record
ord-b9f21036add04e1582d594304b95bbe0
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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