((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

Base Information

• Chemical Name: ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone
• CAS No.: 1612143-64-2
• Molecular Formula: C₂₀H₂₄ClNO₃S
• Molecular Weight: 393.934
• Mol file: 1612143-64-2.mol

Synonyms:((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

Chemical Property of ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone

There total 6 articles about ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone 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: 73.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (1092682-58-0) → ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone (1612143-64-2)

Guidance literature:

With palladium diacetate; In diethyl ether; dichloromethane; at -10 - 20 ℃; diastereoselective reaction;

DOI:10.1016/j.bmc.2016.11.018

Reference yield:

cinnamoyl chloride (35086-79-4,95602-71-4) → ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone (1612143-64-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0 - 20 °C

2: palladium diacetate / dichloromethane; diethyl ether / -10 - 20 °C

With palladium diacetate; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmc.2016.11.018

Reference yield:

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7,940-62-5) → ((1S,2S)-2-(4-chlorophenyl)cyclopropyl)((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)methanone (1612143-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 0 - 20 °C

3: palladium diacetate / dichloromethane; diethyl ether / -10 - 20 °C

With thionyl chloride; palladium diacetate; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmc.2016.11.018

upstream raw materials:

cinnamoyl chloride

(+)-camphorsultam

diazomethane

(E)-3-(4-chlorophenyl)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one

Downstream raw materials:

(+)-(1S,2S)-2-(4-chlorophenyl)cyclopropanecarboxylic acid

tert-butyl ((1S,2R)-2-(4-chlorophenyl)cyclopropyl)carbamate

(1S,2R)-2-(4-chlorophenyl)-N-propylcyclopropan-1-amine

(1S,2R)-2-(4-chlorophenyl)cyclopropan-1-amine