4-Hydroxybenzaldehyde → HCID 22860522、化合物

HRID 488177ノート

反応式

HRID 488177 の反応式
[C:1]1([C@H:7]([NH2:16])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[BH4-].[Na+].[ClH:28]>C(O)C>[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:16][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:20][CH:19]=1.[ClH:28]

参加物

6

反応物 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10138221(R)-alpha-Phenyl-4-methylphenethylamine

生成物 1

HCID 22860522HCID 22860522、化合物収率 64.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

21.13 g (0.1 mole) of (R)-(-)-α-phenyl-β-p-tolylethylamine (optical purity: 100%) and 12.82 g (0.105 mole) of p-hydroxybenzaldehyde were dissolved in 750 ml of ethyl alcohol. The reaction solution thus obtained was stirred at room temperature for 3 hours, and then stirred under reflux for 1 hour. Thereafter, the reaction solution was admixed at room temperature with 1.89 g (0.05 mole) of sodium borohydride, stirred for 3 hours, and then stirred under reflux for 1 hour. The reaction mixture was admixed with 75 ml of a 10% hydrochloric acid, and then concentrated under reduced pressure to give a crude (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine·HCl salt, which was thereafter neutralized with an aqueous sodium hydroxide solution. The resultant solution was concentrated under reduced pressure to obtain the crystals, which were then recrystallized from ethyl alcohol, so that 20.47 g of (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine were obtained as colorless crystals. Yield: 64.5%.

後処理

  1. customThe reaction solution thus obtained
  2. stirringstirred
  3. temperatureunder reflux for 1 hour
  4. stirringstirred for 3 hours
  5. stirringstirred
  6. temperatureunder reflux for 1 hour
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d829edc27d1f44b6a001e63fc7df375e
出典データセット
uspto-grants-1994_03
特許番号
US05298660

反応ノート

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