Sodium Hydroxide → 2-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-ol

HRID 4973

반응식

HRID 4973 반응식
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]2[C:13](=[O:14])[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[C:17]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]2[CH:13]([OH:14])[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4251102-Benzhydryl-3-quinuclidinoneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2984262-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-ol

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
-65 °C

실험 절차

2-(Diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-one (18.9 g) was dissolved in tetrahydrofuran (350 ml), anhydrous) and cooled to -65° C. under nitrogen. Lithium aluminium hydride (1.0 M solution in THF, 40 ml) was added dropwise to the solution which was stirred at room temperature overnight. Water (2 ml) followed by sodium hydroxide (15% 2 ml) and water (6 ml) were added dropwise to the solution resulting in precipitation of the inorganic salts. Magnesium sulfate (2 g) was added and the mixture filtered through celite. The solvent was removed in vacuo and the residue was recrystallised from isopropanol affording the pure cis isomer. The mother liquors were concentrated and found to be 80:20 cis/trans by 1H NMR; this was used in the examples without further purification.

후처리

  1. additionwere added dropwise to the solution
  2. customresulting in precipitation of the inorganic salts
  3. filtrationthe mixture filtered through celite
  4. customThe solvent was removed in vacuo
  5. customthe residue was recrystallised from isopropanol affording the pure cis isomer
  6. concentrationThe mother liquors were concentrated

출처 및 근거

ORD 기록
ord-520e0e99ffeb4242aef88c01c7045ec3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242930

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