Sodium Hydroxide → (2R)-2-phenylpropylamine malate

HRID 420824

反応式

HRID 420824 の反応式
Cl.[C:2]1([CH:8]([CH3:11])[CH2:9][NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:14]([OH:22])(=[O:21])[C@H:15]([CH2:17][C:18]([OH:20])=[O:19])[OH:16]>C(O)C>[C:14]([OH:22])(=[O:21])[CH:15]([CH2:17][C:18]([OH:20])=[O:19])[OH:16].[C:2]1([C@@H:8]([CH3:11])[CH2:9][NH2:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 893322-Phenylpropylamine hydrochlorideHCID 222656L-Malic Acid

生成物 1

HCID 21356831(2R)-2-phenylpropylamine malate収率 118.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
75 °C

実験手順

Charge 2-phenyl-1-propylamine HCl (317.2 g, 1.85 moles), dry ethanol (2.0 L) and NaOH beads (75.4 g, 1.89 moles) washed with additional ethanol (500 mL) to a dry 3-L round bottom flask under nitrogen. Stir the mixture for 1.6 hours. Filter and add a solution of L-malic acid (62.0 g, 0.462 mole, 0.25 equivalents) in ethanol (320 mL) dropwise to the yellow filtrate. Heat the solution to 75° C., then stir at 75° C. for 30 minutes. Remove heat and allow the solution to cool slowly. Allow the resulting thick precipitate to stir overnight. Filter the precipitate, rinse with ethanol (325 mL) and dry under reduced pressure to afford (2R)-2-phenylpropylamine malate (147.6 g, 39.5%) as a white crystalline solid. Chiral GC analysis of the free base, 2-phenyl-1-propylamine reveals 83.2% e.e. enriched in the R-isomer. (Configuration is assigned via spectrometric comparison with commercial 2-phenyl-1-propylamine.) 1H NMR (CDCl3, 300 MHz) δ 7.32 (m, 2H), 7.21 (m, 3H), 2.86 (m, 2H), 2.75 (m, 1H), 1.25 (d, 3H, J=6.9), 1.02 (br s, 2H).

後処理

  1. washwashed with additional ethanol (500 mL) to a dry 3-L round bottom flask under nitrogen
  2. filtrationFilter
  3. stirringstir at 75° C. for 30 minutes
  4. customRemove
  5. temperatureheat
  6. temperatureto cool slowly
  7. stirringto stir overnight
  8. filtrationFilter the precipitate
  9. washrinse with ethanol (325 mL)
  10. customdry under reduced pressure

出典と根拠

ORDレコード
ord-c1eb359aa6e64ed287963ec16ad719bb
出典データセット
uspto-grants-2012_01
特許番号
US08097652B2

関連ノート

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