(3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde

Base Information

• Chemical Name: (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde
• CAS No.: 1443054-71-4
• Molecular Formula: C₁₉H₂₅NO₃S
• Molecular Weight: 347.478
• Mol file: 1443054-71-4.mol

Synonyms:(3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde

Chemical Property of (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde

There total 8 articles about (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde 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: 87.0%

N-(2-cyclohexylideneethyl)-4-methyl-N-(4-oxobutyl)benzenesulfonamide (1443054-37-2) → (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde (1443054-71-4)

Guidance literature:

With disodium hydrogenphosphate; iron(III) trisphenanthroline trisbis(trifluoromethylsulfonyl)amide; (2S,5S)-2-tert-butyl-3-methyl-5-(naphthalen-1-ylmethyl)imidazolidin-4-one trifluoroacetic acid salt; In 1,2-dimethoxyethane; at -30 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja4047312

Reference yield:

N-(4,4-diethoxybutyl)-4-methylbenzenesulfonylamide (858005-68-2) → (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde (1443054-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h

1.2: 18 h

2.1: trifluoroacetic acid / chloroform; water / 3 h

3.1: iron(III) trisphenanthroline trisbis(trifluoromethylsulfonyl)amide; (2S,5S)-2-tert-butyl-3-methyl-5-(naphthalen-1-ylmethyl)imidazolidin-4-one trifluoroacetic acid salt; disodium hydrogenphosphate / 1,2-dimethoxyethane / 12 h / -30 °C / Inert atmosphere

With disodium hydrogenphosphate; iron(III) trisphenanthroline trisbis(trifluoromethylsulfonyl)amide; (2S,5S)-2-tert-butyl-3-methyl-5-(naphthalen-1-ylmethyl)imidazolidin-4-one trifluoroacetic acid salt; sodium hydride; trifluoroacetic acid; In 1,2-dimethoxyethane; chloroform; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ja4047312

Reference yield:

2-cyclohexylidene ethanol (932-89-8) → (3R,4R)-3-cyclohexenyl-1-tosylpiperidine-4-carbaldehyde (1443054-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 3 h / -40 - 20 °C

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h

2.2: 18 h

3.1: trifluoroacetic acid / chloroform; water / 3 h

4.1: iron(III) trisphenanthroline trisbis(trifluoromethylsulfonyl)amide; (2S,5S)-2-tert-butyl-3-methyl-5-(naphthalen-1-ylmethyl)imidazolidin-4-one trifluoroacetic acid salt; disodium hydrogenphosphate / 1,2-dimethoxyethane / 12 h / -30 °C / Inert atmosphere

With disodium hydrogenphosphate; N-chloro-succinimide; dimethylsulfide; iron(III) trisphenanthroline trisbis(trifluoromethylsulfonyl)amide; (2S,5S)-2-tert-butyl-3-methyl-5-(naphthalen-1-ylmethyl)imidazolidin-4-one trifluoroacetic acid salt; sodium hydride; trifluoroacetic acid; In 1,2-dimethoxyethane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ja4047312

upstream raw materials:

N-(4,4-diethoxybutyl)-4-methylbenzenesulfonylamide

p-toluenesulfonyl chloride

ethyl cyclohexylideneacetate

cyclohexanone