Methyl iodide → 2-(2-Methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131399ノート

反応式

HRID 131399 の反応式
[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]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69212205(S)-di-tert-Butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate

生成物 1

HCID 692102832-(2-Methoxyethyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  1. waitAllow the mixture to reach room temperature overnight
  2. extractionextract three times with ethyl acetate
  3. dry with materialdry over sodium sulfate
  4. concentrationconcentrate under reduced pressure
  5. customPurify by flash chromatography
  6. washeluting with a step gradient

出典と根拠

ORDレコード
ord-c34f260e1d414b6393a191aa6b549165
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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