Benzaldehyde → (S)-2-benzylamino-3-phenyl-1-propanol

HRID 23236

反応式

HRID 23236 の反応式
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>C(O)C.[Pt]>[CH2:12]([NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 240BenzaldehydeHCID 447213phenylalaninol, (S)-HCID 178418361HCID 178418361、化合物

生成物 1

HCID 10514267(S)-2-benzylamino-3-phenyl-1-propanol収率 48.1%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

L-Phenylalaninol (5 g, 33 mmoles) and 3.59 g (33.83 mmoles) of benzaldehyde were dissolved in 55 mL of 3A ethanol under inert atmosphere in a Parr shaker and the mixture was warmed to 60° C. for 2.7 hours. The mixture was cooled to approximately 25° C. and 0.99 g of 5% platinum on carbon was added and the mixture was hydrogenated at 60 psi of hydrogen and 40° C. for 10 hours. The catalyst was filtered off, the product was concentrated under reduced pressure and the crude solid product was recrystallized from 150 mL of heptane to give 3.83 g (48% yield) of N-benzyl-L-phenylalaninol as a white solid.

後処理

  1. temperatureThe mixture was cooled to approximately 25° C.
  2. filtrationThe catalyst was filtered off
  3. concentrationthe product was concentrated under reduced pressure
  4. customthe crude solid product was recrystallized from 150 mL of heptane

出典と根拠

ORDレコード
ord-b0413f266656417db402d9d5293f8f55
出典データセット
uspto-grants-2005_02
特許番号
US06849760B2

関連ノート

読み込み中…