Water → 3-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-

HRID 1376207

반응식

HRID 1376207 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C:9](=O)[CH2:10][C@H:11]([OH:17])[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][NH:8][CH2:9][CH2:10][C@@H:11]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[OH:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 10261821(βS)-β-Hydroxy-N-methyl-2-thiophenepropanamideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 100950473-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-수율 95.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1728 ml of dry tetrahydrofuran are initially charged with 52 g of lithium aluminium hydride and heated to reflux. At the same time, dropwise addition of 86.4 g of N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide dissolved in 692 g of tetrahydrofuran is commenced. Once dropwise addition is complete, stirring is continued under reflux overnight. The reaction mixture is then cooled to room temperature and 1037 ml of water are cautiously added dropwise. 173 ml of a 10% sodium hydroxide solution were then added dropwise and the solution was filtered. The solvent was removed under reduced pressure. The crude solution was admixed with 346 ml of 1 N sodium hydroxide solution and extracted 3 times with 345 ml of toluene each time. The organic phases are combined and the volatile constituents are removed under reduced pressure to obtain 76 g of (1S)-3-(methylamino)-1-(2-thienyl)-1-propanol (84% purity, 80% of theory).

후처리

  1. temperatureheated to reflux
  2. additionOnce dropwise addition
  3. temperatureunder reflux overnight
  4. filtrationthe solution was filtered
  5. customThe solvent was removed under reduced pressure
  6. extractionextracted 3 times with 345 ml of toluene each time
  7. customthe volatile constituents are removed under reduced pressure

출처 및 근거

ORD 기록
ord-ead2dfa318114c3daba0c8209e705a63
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169938B2

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