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

HRID 730954

反応式

HRID 730954 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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 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).

後処理

  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

出典と根拠

ORDレコード
ord-a25ca14cade94ddca181561a4669b53e
出典データセット
uspto-grants-2009_09
特許番号
US07582776B2

関連ノート

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