Ethyl Acetate → (S)-3-(3-chloro-phenyl)-N1,N1-dimethyl-propane-1,2-diamine hydrochloride salt

HRID 1879480ノート

反応式

HRID 1879480 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].FC(F)(F)C(O)=O.[NH2:14][C@@H:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[C:16]([N:18]([CH3:20])[CH3:19])=O.C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.CCOCC>[ClH:28].[Cl:28][C:24]1[CH:23]=[C:22]([CH2:21][C@H:15]([NH2:14])[CH2:16][N:18]([CH3:20])[CH3:19])[CH:27]=[CH:26][CH:25]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67153272(S)-2-amino-3-(3-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt

生成物 1

HCID 67153248(S)-3-(3-chloro-phenyl)-N1,N1-dimethyl-propane-1,2-diamine hydrochloride salt収率 130.6%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of lithium aluminum hydride in tetrahydrofuran (3.5 M; 20 mL; 70 mmol) was added cautiously to an ice-bath cooled solution of (S)-2-amino-3-(3-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt (4.00 g, 11.8 mmol) in tetrahydrofuran (20 mL). The reaction mixture was heated at reflux for 4 h, and then cooled. Ethyl acetate and ether were added, and then 3 M sodium hydroxide solution (100 mL) was added. The layers were separated and the aqueous layer was back-extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was taken up in 1 M HCl in ether (20 mL). The resulting white precipitate was stirred for 1 h, and then filtered to give (S)-3-(3-chloro-phenyl)-N1,N1-dimethyl-propane-1,2-diamine hydrochloride salt (1.92 g, 57%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. temperaturecooled
  4. customThe layers were separated
  5. extractionthe aqueous layer was back-extracted with ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-b2b202aeca494a449ec4b39e4c4212ac
出典データセット
uspto-grants-2012_11
特許番号
US08314250B2

反応ノート

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