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

HRID 1034745ノート

反応式

HRID 1034745 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 602052351-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6c153044c92842159d561f886a96ca6d
出典データセット
uspto-grants-2013_10
特許番号
US08545897B2

反応ノート

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