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

HRID 1440817

반응식

HRID 1440817 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3735a51e5a52426badb63417619f805d
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05500443

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