Ammonium Chloride → 1-Benzyl-3-[2-(2,4-difluorophenyl)-2-hydroxyethyl]pyrrolidine

HRID 1440817

反応式

HRID 1440817 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[F:16][C:17]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][CH:19]([C:18]2[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:17]=2[F:16])[OH:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 737702,4-DifluorobenzaldehydeHCID 5462224MagnesiumHCID 123645181-Benzyl-3-(chloromethyl)pyrrolidine

生成物 1

HCID 189821971-Benzyl-3-[2-(2,4-difluorophenyl)-2-hydroxyethyl]pyrrolidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution containing 0.38 mol of 1-benzyl-3-chloromethylpyrrolidine in 200 ml of tetrahydrofuran (THF) is added, at 65° C., to a suspension containing 9.3 g of magnesium in 100 ml of THF. The mixture is maintained at reflux and, after disappearance of the metal, followed by cooling, this solution is added to a solution containing 0.38 mol of 2,4-difluorobenzaldehyde in 300 ml of THF. The mixture is maintained at room temperature for 12 hours and is then hydrolyzed with 220 ml of saturated ammonium chloride solution. After extraction with dichloromethane and then evaporation, the residual oil is purified by chromatography on a column of silica, using a dichloromethane/methanol/aqueous ammonia (98/2/0.2) mixture as eluent, and gives the expected product.

後処理

  1. additionis added, at 65° C., to a suspension
  2. temperatureThe mixture is maintained
  3. temperatureat reflux
  4. temperatureby cooling
  5. additionthis solution is added to a solution
  6. extractionAfter extraction with dichloromethane
  7. customevaporation
  8. customthe residual oil is purified by chromatography on a column of silica

出典と根拠

ORDレコード
ord-3735a51e5a52426badb63417619f805d
出典データセット
uspto-grants-1996_03
特許番号
US05500443

関連ノート

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