Sodium Hydroxide → 1-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine

HRID 1633575ノート

反応式

HRID 1633575 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.CCOC(C)=O.O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 2

HCID 14798Sodium HydroxideHCID 15512819HCID 15512819、化合物

生成物 1

HCID 155128201-Benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine収率 65.2%

試薬・触媒・溶媒 4

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-4-hydroxypiperidine (1.01 g 3.20 mmole) in acetic acid (40 mL) at room temperature was added 2 drops of concentrated sulfuric acid. The resulting solution was heated to reflux, and the mixture stirred for 2 days. The mixture was cooled to room temperature and diluted with EtOAc (100 mL) and water (100 mL). The solution was basified with 50% NaOH solution until pH=10. The layers were separated and the organics washed with brine. The combined aqueous layers were extracted three times with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography (elution with 1:1 EtOAc-hexane) to give 0.62 g (65%) of 1-benzyl-4-(5-fluoro-2-methoxy-phenyl)-1,2,5,6-tetrahydropyridine as a yellow oil.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. customThe layers were separated
  4. washthe organics washed with brine
  5. extractionThe combined aqueous layers were extracted three times with EtOAc (50 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. washFlash chromatography (elution with 1:1 EtOAc-hexane)

出典と根拠

ORDレコード
ord-45255cc203724c07a4616fce7af15b9a
出典データセット
uspto-grants-2003_01
特許番号
US06503928B2

反応ノート

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