(1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one

Base Information

• Chemical Name: (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one
• CAS No.: 876760-58-6
• Molecular Formula: C₁₇H₂₂N₂O₃S
• Molecular Weight: 334.439

Synonyms:(1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one

Chemical Property of (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one

Chemical Property:

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Technology Process of (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one

There total 4 articles about (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one 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: 75.0%

(1S,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.01,5]dec-4-en-2-one (876760-57-5) → (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.01,5]decan-2-one (876760-58-6)

Guidance literature:

With sodium cyanoborohydride; acetic acid; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2005.10.042

Reference yield:

2-(2-tosylhydrazono)-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid (876760-56-4) → (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.01,5]decan-2-one (876760-58-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / thionyl chloride / ethyl acetate / 4 h / Heating

2: 75 percent / AcOH; NaBH₃CN / 0.5 h / 20 °C

With thionyl chloride; sodium cyanoborohydride; acetic acid; In ethyl acetate;

DOI:10.1016/j.tet.2005.10.042

Reference yield:

(1S)-(+)-ketopinic acid (464-78-8,6994-94-1,64234-14-6,40724-67-2) → (1S,5R,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.01,5]decan-2-one (876760-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / CH₂Cl₂ / 4 h / 20 °C

2: 90 percent / thionyl chloride / ethyl acetate / 4 h / Heating

3: 75 percent / AcOH; NaBH₃CN / 0.5 h / 20 °C

With thionyl chloride; sodium cyanoborohydride; acetic acid; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tet.2005.10.042

upstream raw materials:

(1S,7R)-10,10-Dimethyl-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]dec-4-en-2-one

2-(2-tosylhydrazono)-7,7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acid

(1S)-(+)-ketopinic acid

toluene-4-sulfonic acid hydrazide

Downstream raw materials:

1-(1-Acetyl-1H-indol-3-yl)-2-[(1S,5R,7R)-10,10-dimethyl-2-oxo-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]dec-4-yl]-ethane-1,2-dione

1-[(1S,5R,7R)-10,10-Dimethyl-2-oxo-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]dec-4-yl]-2-thiophen-2-yl-ethane-1,2-dione

1-[(1S,5R,7R)-10,10-Dimethyl-2-oxo-3-(toluene-4-sulfonyl)-3,4-diaza-tricyclo[5.2.1.0^1,5]dec-4-yl]-butane-1,2-dione

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