Methyl iodide → 1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

HRID 408256노트

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HRID 408256 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][C:12]1([C:27]([O-:29])=[O:28])[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13]1.[CH3:30]I.[Cl-].[NH4+]>C1COCC1>[CH3:11][C:12]1([C:27]([O:29][CH3:30])=[O:28])[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 602052331-Benzyl 3-methylpyrrolidine-1,3-dicarboxylate

생성물 1

HCID 602052351-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Lithium bis(trimethylsilyl)amide (16.4 mL, 16.4 mmol) was added to 1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate (3.45 g, 13.1 mmol) in THF (20 mL) at −78° C., and the reaction was stirred at −78° C. for 20 minutes. MeI (1.10 mL, 17.7 mmol) was added, and the reaction was warmed to room temperature. After 2 hours at room temperature, the mixture was poured onto saturated ammonium chloride (20 mL), extracted with ether, washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (hexane:ethyl acetate, 4:1) to give 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 75% yield) as an oil.

후처리

  1. temperaturethe reaction was warmed to room temperature
  2. waitAfter 2 hours at room temperature
  3. extractionextracted with ether
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. customthe residue was purified by chromatography (hexane:ethyl acetate, 4:1)

출처 및 근거

ORD 기록
ord-17c05f7dd96043e9b6486a38064e2514
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08758830B2

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