Tetrahydrofuran → N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine

HRID 868138노트

반응식

HRID 868138 반응식
[CH3:1][N:2]([CH3:18])[C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=O.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][N:2]([CH3:18])[CH2:3][CH:5]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 14798Sodium HydroxideHCID 14280891N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14280892N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine수율 58.2%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A solution of 2.91 g (11.8 mmol) N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide and 15 ml anhydrous tetrahydrofuran was dropped into a suspension of 1.41 g (35 mmol) lithium aluminum hydride and 30 ml tetrahydrofuran. The reaction was refluxed overnight then cooled to room temperature. To the solution was added 1.5 ml water, 1.5 ml 15% sodium hydroxide and 4.5 ml of water. The resulting precipitate was filtered. The filtrate was concentrated under reduced pressure, dissolved in dichlromethane, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue was bulb to bulb distilled giving 1.5 g (58%) of N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as a clear liquid. This material was used in the next step.

후처리

  1. temperatureThe reaction was refluxed overnight
  2. filtrationThe resulting precipitate was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutiondissolved in dichlromethane
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated under reduced pressure
  7. distillationdistilled

출처 및 근거

ORD 기록
ord-6a6fdd4978f347cfa69b5d30c01bdb8f
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04777175

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