(R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

Base Information

• Chemical Name: (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate
• CAS No.: 1542148-01-5
• Molecular Formula: C₂₀H₂₁NO₂
• Molecular Weight: 307.392
• Mol file: 1542148-01-5.mol

Synonyms:(R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

Chemical Property of (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

There total 8 articles about (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate 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: 93.0%

2-Picolinic acid (98-98-6) + C14H18O (1542147-99-8) → (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate (1542148-01-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h; diastereospecific reaction; Cooling with ice;

DOI:10.1021/ol403472y

Reference yield:

C14H18O (1542147-96-5) → (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate (1542148-01-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Molecular sieve

2: (S)-diphenylprolinol; Trimethyl borate; N,N-diethylaniline borane / tetrahydrofuran / 2 h / 0 - 5 °C

3: dicyclohexyl-carbodiimide; dmap / dichloromethane / 2 h / 20 °C / Cooling with ice

With dmap; N,N-diethylaniline borane; tetrapropylammonium perruthennate; Trimethyl borate; (S)-diphenylprolinol; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol403472y

Reference yield:

cyclohexenone (930-68-7) → (R)-1-((S)-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate (1542148-01-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: bromine; triethylamine / dichloromethane / 0.08 h / 0 °C

2.1: (S)-diphenylprolinol; Trimethyl borate; N,N-diethylaniline borane / tetrahydrofuran / 19.17 h / -10 - 20 °C

3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 1 h / 20 °C

4.1: tetrahydrofuran / 1 h / 0 °C

5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C

5.2: 1 h / -78 - 0 °C

6.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C / Molecular sieve

7.1: (S)-diphenylprolinol; Trimethyl borate; N,N-diethylaniline borane / tetrahydrofuran / 2 h / 0 - 5 °C

8.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 2 h / 20 °C / Cooling with ice

With dmap; N,N-diethylaniline borane; tetrapropylammonium perruthennate; Trimethyl borate; (S)-diphenylprolinol; bromine; tert.-butyl lithium; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1021/ol403472y

upstream raw materials:

C₁₄H₁₈O

cyclohexenone

(R)-2-bromocyclohex-2-en-1-yl picolinate

(1R)-2-bromocyclohex-2-en-1-ol

Downstream raw materials:

[(1R,3R,Z)-2-ethylidene-3-methylcyclohexyl]benzene

[(1R,3R,Z)-3-butyl-2-ethylidenecyclohexyl]benzene

(2S,6S)-2,6-diphenylcyclohexanone

(2R,6S)-2-methyl-6-phenylcyclohexanone