Iodoethane → (2R)-1-(tert-butoxycarbonyl)-4-ethylpiperazine-2-carboxylic acid

HRID 603190Notes

Reaction equation

HRID 603190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[CH2:23](I)[CH3:24]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][CH3:24])[CH2:10][C@@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 24820285(2R)-1-(tert-Butoxycarbonyl)piperazine-2-carboxylic acid

Product 1

HCID 59846012(2R)-1-(tert-butoxycarbonyl)-4-ethylpiperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (2R)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.406 g) and Na2CO3 (2.59 g) was added dry EtOH (28 ml) then ethyl iodide (0.54 ml) and the mixture heated at reflux for 18 h under argon. The solvent was then removed under reduced pressure and 5% MeOH/DCM (40 ml) was added and stirred for 1 hour in a sealed flask. The solution was filtered and washed with dichloromethane (2×10 mL). The filtrate was then placed directly onto a 120 g-silica cartridge and was purified using eluent 10-70% MeOH/DCM. After evaporation, the product was isolated as a white foam (1.00 g), which was used without further purification.

Workup

  1. temperatureat reflux for 18 h under argon
  2. customThe solvent was then removed under reduced pressure and 5% MeOH/DCM (40 ml)
  3. additionwas added
  4. filtrationThe solution was filtered
  5. washwashed with dichloromethane (2×10 mL)
  6. customwas purified
  7. customAfter evaporation

Sources & evidence

ORD record
ord-aae2b92613da4217a401a877e4a70050
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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