(1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane
• CAS No.: 169215-46-7
• Molecular Formula: C₁₅H₂₁NO₂S
• Molecular Weight: 279.403

Synonyms:(1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane

Chemical Property of (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane

Chemical Property:

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Technology Process of (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane

There total 3 articles about (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane 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: 7.0%

[N-(p-tolylsulfonyl)imino]phenyliodinane (55962-05-5) + (3R,6R)-trans-3,6-dimethylcyclohexene (169275-20-1) → (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane (169215-46-7)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate);

DOI:10.1246/cl.1995.337

Reference yield:

(3R,6R)-trans-3,6-dimethylcyclohexene (169275-20-1) → (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane (169215-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / ICl, NaN₃

2: 1.) LAH, 2.) Et₃N

With lithium aluminium tetrahydride; sodium azide; Iodine monochloride; triethylamine;

DOI:10.1246/cl.1995.337

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + (1R,2R,3R,4R)-2-Azido-3-iodo-1,4-dimethyl-cyclohexane (169215-47-8) → (1R,2R,5R,6S)-2,5-Dimethyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane (169215-46-7)

Guidance literature:

With lithium aluminium tetrahydride; triethylamine; Yield given. Multistep reaction;

DOI:10.1246/cl.1995.337

upstream raw materials:

[N-(p-tolylsulfonyl)imino]phenyliodinane

(3R,6R)-trans-3,6-dimethylcyclohexene

p-toluenesulfonyl chloride

(1R,2R,3R,4R)-2-Azido-3-iodo-1,4-dimethyl-cyclohexane

Downstream raw materials:

(1R,2R,3R,6R)-3,6-dimethylcyclohexane-1,2-diamine

C₂₂H₃₀N₂O₄S₂

N-((1R,2R,3R,6R)-2-Azido-3,6-dimethyl-cyclohexyl)-4-methyl-benzenesulfonamide

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