Iodoethane → (S)-2-(2-ethoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131402Notes

Reaction equation

HRID 131402 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@@H:11]1[CH2:23][CH2:24][OH:25])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:26](I)[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@@H:11]1[CH2:23][CH2:24][O:25][CH2:26][CH3:27])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69212205(S)-di-tert-Butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate

Product 1

HCID 69215264(S)-2-(2-ethoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add sodium hydride (0.558 g, 14.0 mmol) in portions to (S)-2-(2-hydroxyethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.075 g, 9.31 mmol) in dimethylformamide (60 mL) and stir for 15 minutes. Cool to 0° C. and add ethyl iodide (1.5 mL, 18.6 mmol) dropwise and stir at 0° C. After 30 minutes warm the mixture to room temperature and stir overnight. Dilute the mixture with ethyl acetate and wash the organics six times with brine. Dry over sodium sulfate and concentrate under reduced pressure to give (S)-2-(2-ethoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.17 g, 95%) as a yellow oil.

Workup

  1. stirringstir at 0° C
  2. temperatureAfter 30 minutes warm the mixture to room temperature
  3. stirringstir overnight
  4. washwash the organics six times with brine
  5. dry with materialDry over sodium sulfate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-3a354046263f44e285285b7939b1016d
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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