(1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester
• CAS No.: 211503-87-6
• Molecular Formula: C₃₂H₃₅ClN₂O₃
• Molecular Weight: 531.094
• Mol file: 211503-87-6.mol

Synonyms:(1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester

Chemical Property of (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester

There total 7 articles about (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester 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: 20.0%

2-chloro-5-(1,5-cyclohexadienyl)pyridine (211503-84-3) + ({(1S,2R,5S)-5-methyl-2-[1-methyl-1-(2-naphthyl)ethyl]cyclohexyl}oxy)carbonylhydroxylamine (211503-82-1) → (1S,4R)-6-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester + (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester (211503-87-6) + (1R,4S)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(98)00803-X

Reference yield:

2-choro-5-iodopyridine (69045-79-0) → (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester (211503-87-6)

Guidance literature:

Multi-step reaction with 2 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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; magnesium; dimethyl sulfoxide; triethylamine;

DOI:10.1021/jo9813078

Reference yield:

(+)-8-(2-naphthyl)menthol (211503-80-9) → (1S,4R)-5-(6-Chloro-pyridin-3-yl)-2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene-3-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-naphthalen-2-yl-ethyl)-cyclohexyl ester (211503-87-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridine, 2.) pyridine, N,O-bis(trimethylsilyl)hydroxylamine / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 2 h

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

With pyridine; oxalyl dichloride; N,O-bis(trimethylsilyl)hydroxylamine; dimethyl sulfoxide; triethylamine;

DOI:10.1021/jo9813078

upstream raw materials:

2-chloro-5-(1,5-cyclohexadienyl)pyridine

({(1S,2R,5S)-5-methyl-2-[1-methyl-1-(2-naphthyl)ethyl]cyclohexyl}oxy)carbonylhydroxylamine

2-choro-5-iodopyridine

2-bromocyclohexa-1,3-diene

Downstream raw materials:

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

(-)-tert-butyl N-[(1R,2R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohexyl]carbamate

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

epibatidine