Water → 2-(((1-Benzylpyrrolidin-3-yl)methyl)amino)ethanol

HRID 620860

반응식

HRID 620860 반응식
[OH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:11][C:10](=O)[N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:14]1([CH2:13][N:9]2[CH2:10][CH2:11][CH:7]([CH2:5][NH:4][CH2:3][CH2:2][OH:1])[CH2:8]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 14280883N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 142808882-(((1-Benzylpyrrolidin-3-yl)methyl)amino)ethanol수율 76.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 46.6 g (0.18 mole) of N-(2-hydroxyethyl)-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide in 200 ml of tetrahydrofuran was added dropwise to a slurry of 20.25 g (0.534 mole) of lithium aluminum hydride in 150 ml tetrahydrofuran. The reaction was refluxed three hours, then cooled in an ice bath. The work up consisted of sequential addition of 20 ml water, 20 ml 15% sodium hydroxide then 60 ml water. The reaction was filtered and the precipitate washed with ethanol. The filtrate was concentrated at reduced pressure, the residue taken up in dichloromethane, dried over magnesium sulfate, and the solvent removed at reduced pressure to give 32.31 g of 2-[[[1-(phenylmethyl)-3-pyrrolidinyl]methyl]amino]ethanol as an oil. This material was used in the next step without further purification.

후처리

  1. temperatureThe reaction was refluxed three hours
  2. temperaturecooled in an ice bath
  3. filtrationThe reaction was filtered
  4. washthe precipitate washed with ethanol
  5. concentrationThe filtrate was concentrated at reduced pressure
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed at reduced pressure

출처 및 근거

ORD 기록
ord-b4aa529f5f0b48afab8a59c9d9495d34
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822801

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