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

HRID 131399노트

반응식

HRID 131399 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c34f260e1d414b6393a191aa6b549165
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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