(2R)-2α-(Diphenylmethyl)-N-(2-methoxybenzyl)-1-azabicyclo[2.2.2]octan-3α-amine

Base Information

• Chemical Name: (2R)-2α-(Diphenylmethyl)-N-(2-methoxybenzyl)-1-azabicyclo[2.2.2]octan-3α-amine
• CAS No.: 135095-42-0
• Molecular Formula: C₂₈H₃₂N₂O
• Molecular Weight: 412.575
• Mol file: 135095-42-0.mol

Synonyms:

Chemical Property of (2R)-2α-(Diphenylmethyl)-N-(2-methoxybenzyl)-1-azabicyclo[2.2.2]octan-3α-amine

Chemical Property:

• PSA: 24.50000
• LogP: 5.40850

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2α-(Diphenylmethyl)-N-(2-methoxybenzyl)-1-azabicyclo[2.2.2]octan-3α-amine

There total 12 articles about (2R)-2α-(Diphenylmethyl)-N-(2-methoxybenzyl)-1-azabicyclo[2.2.2]octan-3α-amine 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: 72.6%

(-)-cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-amine (32531-19-4,32531-24-1,129912-96-5,141958-06-7,142035-23-2) + ortho-anisaldehyde (135-02-4) → (2S,3S)-cis-2-(diphenylmethyl)-N-[(2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine (129912-34-1,132746-60-2,134731-58-1,135095-42-0,142035-22-1)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jm00092a009

Reference yield: 22.0%

2-(diphenylmethyl)-N-<(2-methoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-imine (141958-08-9) → (+/-)-CP 93846 (129912-34-1,132746-60-2,134731-58-1,135095-42-0,142035-22-1)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 24h; Ambient temperature;

DOI:10.1021/jm00092a009

Reference yield:

2-(4,4'-Dibrombenzhydryl)-3-chinuclidinon (24802-70-8) → (2S,3S)-cis-2-(diphenylmethyl)-N-[(2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine (129912-34-1,132746-60-2,134731-58-1,135095-42-0,142035-22-1)

Guidance literature:

Multi-step reaction with 5 steps

1: camphorsulfonic acid / toluene / 18 h / Heating

2: 9-BBN / tetrahydrofuran / 72 h / Ambient temperature

3: 48percent HBr / 2 h / 130 - 140 °C

4: 49.5 percent / 6N HCl, H₂ / 10percent Pd/C / ethanol / 7 h / 2068.6 Torr

5: 72.6 percent / 2N HCl, sodium cyanoborohydride / methanol / 24 h / Ambient temperature

With hydrogenchloride; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; hydrogen bromide; hydrogen; sodium cyanoborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jm00092a009

upstream raw materials:

(-)-cis-2-(diphenylmethyl)-1-azabicyclo<2.2.2>octan-3-amine

ortho-anisaldehyde

2-(4,4'-Dibrombenzhydryl)-3-chinuclidinon

cis-2--N-<3-(4-methoxyphenyl)methyl>-1-azabicyclo<2.2.2>octan-3-amine

Downstream raw materials:

(-)-(2S,3S)-cis-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octane-3-amine

cis-2-(diphenylmethyl)-N-<(2-methoxyphenyl)methyl>-N-methyl-1-azabicyclo<2.2.2>octan-3-amine

Refernces

• 1、 -. "Use of NK-1 receptor antagonists for the manufacture of a medicament in the treatment of symptoms of irritable bowel syndrome". . . Retrieved 2008/06/13.