(1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane

Base Information

• Chemical Name: (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane
• CAS No.: 1299472-55-1
• Molecular Formula: C₈H₁₁Cl₃INO₂
• Molecular Weight: 386.444
• Mol file: 1299472-55-1.mol

Synonyms:(1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane

Chemical Property of (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane

There total 7 articles about (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane 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: 76.0%

C8H9Cl3INO (1299472-54-0) → (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane (1299472-55-1)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 0.75h;

DOI:10.1039/c0ob00619j

Reference yield:

ethyl (2E)-2,7-octadienoate (55282-91-2) → (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane (1299472-55-1)

Guidance literature:

Multi-step reaction with 6 steps

1: diisobutylaluminium hydride / diethyl ether; hexane / -78 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3: di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium / dichloromethane / 72 h / 45 °C / Inert atmosphere

4: Grubbs catalyst first generation / dichloromethane / 65 °C

5: N-iodo-succinimide / chloroform / 18 h / Inert atmosphere

6: hydrogenchloride; water / methanol / 0.75 h / 20 °C

With Grubbs catalyst first generation; hydrogenchloride; N-iodo-succinimide; di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium; water; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; hexane; dichloromethane; chloroform; 3: Overman rearrangement;

DOI:10.1039/c0ob00619j

Reference yield:

(2E)-octa-2,7-dien-1-ol (62179-18-4) → (1S,2S,3S)-1-(2',2',2'-trichloromethylcarbonylamino)-2-hydroxy-3-iodocyclohexane (1299472-55-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2: di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium / dichloromethane / 72 h / 45 °C / Inert atmosphere

3: Grubbs catalyst first generation / dichloromethane / 65 °C

4: N-iodo-succinimide / chloroform / 18 h / Inert atmosphere

5: hydrogenchloride; water / methanol / 0.75 h / 20 °C

With Grubbs catalyst first generation; hydrogenchloride; N-iodo-succinimide; di-μ-chlorobis[(η(5)-(S)-(pR)-2-(2'-(4'-(1-methylethyl))oxazolinyl)cyclopentadienyl, 1-C, 3'-N)(η(4)-tetraphenylcyclobutadiene)cobalt]dipalladium; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; chloroform; 2: Overman rearrangement;

DOI:10.1039/c0ob00619j

upstream raw materials:

5-Hexen-1-ol

C₈H₉Cl₃INO

(2E)-octa-2,7-dien-1-ol

ethyl (2E)-2,7-octadienoate