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

HRID 497921노트

반응식

HRID 497921 반응식
[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

참가 물질

7

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 517044Potassium AcetateHCID 102245361-Benzyl-4-(4-fluorophenyl)-l-azoniabicyclo[3.1.1]hept-3-ene trifluoromethanesulphonate

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매4회HCID 3776Isopropanol용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1026a31f2d754856a47802297b409b3e
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949650B2

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