Methyl iodide → 2-(2-Methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester
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].[CH3:26]I>O1CCCC1.[Cl-].[NH4+]>[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][CH:11]1[CH2:23][CH2:24][O:25][CH3:26])=[O:9])([CH3:6])([CH3:5])[CH3:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Add sodium hydride (0.675 g, 16.9 mmol) in portions to a 0° C. solution of (S)-2-(2-hydroxyethyl)piperazine-1,4-dicarboxylic acid di-tert-butyl ester (3.72 g, 11.3 mmol) in tetrahydrofuran (50 mL) and stir. After 20 minutes, add methyl iodide (1.4 mL, 22.5 mmol) dropwise. Allow the mixture to reach room temperature overnight, dilute with saturated ammonium chloride and extract three times with ethyl acetate. Combine the organic layers, dry over sodium sulfate and concentrate under reduced pressure. Purify by flash chromatography, eluting with a step gradient starting with dichloromethane up to 7% 2N ammonia-methanol in dichloromethane to obtain 2-(2-methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester.
Workup
- waitAllow the mixture to reach room temperature overnight
- extractionextract three times with ethyl acetate
- dry with materialdry over sodium sulfate
- concentrationconcentrate under reduced pressure
- customPurify by flash chromatography
- washeluting with a step gradient
Sources & evidence
- ORD record
- ord-c34f260e1d414b6393a191aa6b549165
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07384934B2
Reaction notes
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