(R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate

Base Information

• Chemical Name: (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate
• CAS No.: 88000-61-7
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 88000-61-7.mol

Synonyms:(R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate

Chemical Property of (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate

There total 16 articles about (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

(R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-α-hydroxy-α-(4-nitrophenyl)-α-phenyl acetate (126828-59-9) → (R)-(-)-1-azabicyclo<2.2.2>oct-3-yl-(S)-(-)-α-hydroxy-α-(4-aminophenyl)-α-phenyl acetate (88000-61-7)

Guidance literature:

With hydrogen; palladium-polyethylenimine; In methanol; for 48h; under 2280 Torr; Ambient temperature;

DOI:10.1002/jps.2600781011

Reference yield:

ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate (81039-78-3) + (S)-quinuclidin-3-ol (3684-26-2,25333-42-0,34583-34-1,1619-34-7) → (S)-(+)-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate (81039-90-9,88000-56-0,88000-57-1,88000-61-7,88000-62-8)

Guidance literature:

With sodium; Yield given. Multistep reaction; 1.) benzene, reflux, 0.5 h, 2.) benzene, reflux, 24 h;

DOI:10.1021/jm00368a009

Reference yield:

4-nitrobenzophenone (1144-74-7) → (S)-(+)-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-(4-aminophenyl)-α-phenylacetate (81039-90-9,88000-56-0,88000-57-1,88000-61-7,88000-62-8)

Guidance literature:

Multi-step reaction with 5 steps

1: ZnI₂ / CH₂Cl₂ / 72 h / Ambient temperature

2: 3 N aq. HCl / 24 h / Ambient temperature

3: 1.) K₂CO₃, dicyclohexano-18-crown-6 / 1.) acetonitrile, RT, 0.5 h, 2.) acetonitrile, RT, 96 h

4: 100 percent / H₂ / Pd-polyethylamine / methanol / 24 h / 2280 Torr

5: 1.) Na / 1.) benzene, reflux, 0.5 h, 2.) benzene, reflux, 24 h

With hydrogenchloride; perhydrodibenzo-18-crown-6; hydrogen; sodium; potassium carbonate; zinc(II) iodide; Pd-polyethylamine; In methanol; dichloromethane;

DOI:10.1021/jm00368a009

upstream raw materials:

ethyl α-hydroxy-α-(4-aminophenyl)-α-phenylacetate

(S)-quinuclidin-3-ol

4-nitrobenzophenone

1-(4-aminophenyl)-2-phenylethane-1,2-dione

Downstream raw materials:

(R)-(-)-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>pheny>-α-phenylacetate

(S)-(+)-1-azabicyclo<2.2.2>oct-3-yl (RS)-α-hydroxy-α-<4-<2-(3-methylpiperidin-1-yl)-1,2-diazaethylen-1-yl>pheny>-α-phenylacetate