(1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine

Base Information

• Chemical Name: (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine
• CAS No.: 217323-82-5
• Molecular Formula: C₁₁H₁₄BrClN₂
• Molecular Weight: 289.603
• Mol file: 217323-82-5.mol

Synonyms:(1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine

Chemical Property of (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine

There total 38 articles about (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine 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: 96.0%

N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide (211503-92-3) → (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine (217323-82-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jo9813078

Reference yield:

(-)-tert-butyl N-[(1R,2R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohexyl]carbamate (211503-91-2) → (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine (217323-82-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

2: 84 percent / LiBr / tetrahydrofuran / 36 h / Heating

3: 91 percent / CF₃COOH / CH₂Cl₂ / 1 h / 25 °C

With triethylamine; trifluoroacetic acid; lithium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol016420q

Reference yield:

2-choro-5-iodopyridine (69045-79-0) → (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine (217323-82-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) magnesium, 2.) (Ph₃P)4Pd / 1.) THF, 2.) THF, benzene, room temperature, 10 h

2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C

3: 81 percent / hydrogen / PtO₂ / dioxane / 20 h / 760 Torr / Ambient temperature

4: 1.) LiH₂NBH₃, 2.) Na₂CO₃ / 1.) THF, hexane, room temperature, 3 h, 2.) THF, hexane, water, CHCl₃, room temperature, 1 h

5: 85 percent / molybdenum hexacarbonyl / acetonitrile; H₂O / 3 h / Heating

6: 42 percent / triphenylphosphine, carbon tetrabromide / acetonitrile / 0.75 h / 70 °C

7: 96 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; carbon tetrabromide; lithium amidotrihydroborate; molybdenum hexacarbonyl; hydrogen; sodium carbonate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; platinum(IV) oxide; In 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo9813078

upstream raw materials:

N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide

3-[(2E)-3-(6-chloro(3-pyridyl))prop-2-enoyl](4R)-4-benzyl-1,3-oxazolidin-2-one

6-Chloro-3-pyridinecarboxylic acid

6-chloronicotinylaldehyde

Downstream raw materials:

epibatidine

Refernces

• 1、 Boyd, Derek R.,Sharma, Narain D.,Kaik, Magdalena,McIntyre, Peter B. A.,Stevenson, Paul J.,Allen, Christopher C. R.. "Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine". . p. 2774 - 2779,6. Retrieved 2020/08/31.
• 2、 Aoyagi, Sakae,Tanaka, Ryuta,Naruse, Masaichi,Kibayashi, Chihiro. "Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral n-acylnitroso dienophile". . p. 8397 - 8406. Retrieved 2007/10/03.