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

HRID 4973

反応式

HRID 4973 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-520e0e99ffeb4242aef88c01c7045ec3
出典データセット
uspto-grants-1993_09
特許番号
US05242930

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