Water → (+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

HRID 497921ノート

反応式

HRID 497921 の反応式
[C:1]([O-:4])(=O)[CH3:2].[K+].FC(F)(F)S([O-])(=O)=O.[CH2:14]([N+:21]12CC([CH2:26]1)[C:24]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[CH:23][CH2:22]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(O)C>[CH2:14]([N:21]1[CH2:22][CH:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH:2]([CH2:1][OH:4])[CH2:26]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 517044Potassium AcetateHCID 102245361-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

生成物 1

HCID 9912522(+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒4 回HCID 3776Isopropanol溶媒2 回

実験手順

Potassium acetate (0.14 g) was added to a stirred solution of 1-benzyl-4-(4-fluorophenyl)-1-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate (0.5 g) in toluene (2.5 ml) and propan-2-ol (2.5 ml). The mixture was then boiled and stirred under reflux for 24 hours. The mixture was cooled to room temperature and toluene (10 ml) and water (5 ml) were added. The organic layer was separated, dried and evaporated to leave an oil. A solution of the oil in propan-2-ol (2 ml) and toluene (2 ml) was treated with 4M-NaOH (0.4 ml). The mixture was boiled under reflux for 2 hours then cooled to room temperature. Water (5 ml) and toluene 95 ml) were added. The organic layer was separated, washed with water (2×5 ml) and evaporated to give (+,−)-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (ee 5.48%).

後処理

  1. temperatureunder reflux for 24 hours
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customto leave an oil
  6. temperatureunder reflux for 2 hours
  7. temperaturethen cooled to room temperature
  8. customThe organic layer was separated
  9. washwashed with water (2×5 ml)
  10. customevaporated

出典と根拠

ORDレコード
ord-1026a31f2d754856a47802297b409b3e
出典データセット
uspto-grants-2005_09
特許番号
US06949650B2

反応ノート

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