(1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-one

Base Information

• Chemical Name: (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-one
• CAS No.: 117416-31-6
• Molecular Formula: C₂₀H₂₃NO₃S
• Molecular Weight: 357.474

Synonyms:(1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-one

Chemical Property of (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-one

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Technology Process of (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-one

There total 9 articles about (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.0^1,5]dodecan-11-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: 92.0%

rel-(1R,2R)-10-vinylidene-11-azatricyclo<4.4.2.02,6>dodecan-12-one (117416-28-1) + p-toluenesulfonyl chloride (98-59-9) → (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.01,5]dodecan-11-one (117416-31-6)

Guidance literature:

With sodium hydride; In diethyl ether; 1.) reflux, 1 h; 2.) 5 h, room temperature;

DOI:10.1016/S0040-4020(01)86638-2

Reference yield:

Methanesulfonic acid 6-trimethylsilanyl-hex-4-ynyl ester (97997-94-9) → (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.01,5]dodecan-11-one (117416-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium iodide / dimethylformamide / 17 h / 80 °C

2: 87 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

3: 98 percent / formic acid / 0.1 h / Ambient temperature

4: 100 percent / 2 M tetrabutylammonium fluoride / tetrahydrofuran / 1.) 10 min, 0 deg C; 2.) 30 min, room temperature

5: 92 percent / 1.) NaH / diethyl ether / 1.) reflux, 1 h; 2.) 5 h, room temperature

With formic acid; tetrabutyl ammonium fluoride; sodium hydride; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86638-2

Reference yield:

6-iodo-1-(trimethylsilyl)-2-hexyne (88996-02-5) → (1R,5R,6R)-12-(Toluene-4-sulfonyl)-7-vinylidene-12-aza-tricyclo[4.4.2.01,5]dodecan-11-one (117416-31-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

2: 98 percent / formic acid / 0.1 h / Ambient temperature

3: 100 percent / 2 M tetrabutylammonium fluoride / tetrahydrofuran / 1.) 10 min, 0 deg C; 2.) 30 min, room temperature

4: 92 percent / 1.) NaH / diethyl ether / 1.) reflux, 1 h; 2.) 5 h, room temperature

With formic acid; tetrabutyl ammonium fluoride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4020(01)86638-2

upstream raw materials:

rel-(1R,2R)-10-vinylidene-11-azatricyclo<4.4.2.0^2,6>dodecan-12-one

p-toluenesulfonyl chloride

Methanesulfonic acid 6-trimethylsilanyl-hex-4-ynyl ester

1-(Trimethylsilyl)-2-hexyn-6-ol

Downstream raw materials:

N-<<1,2,3,3a,4,5,6,8a-octahydro-7-<1-(trimethylsilylmethyl)-ethenyl>-3a-trans-azulenyl>carbonyl>-p-toluenesulfonamide

N-<<1,2,3,3a,4,5,6,8a-octahydro-7-(1-methylethenyl)-3a-trans-azulenyl>carbonyl>-p-toluenesulfonamide

N-<<1,2,3,3a,4,5,6,8a-octahydro-7-(1-phenylethenyl)-3a-trans-azulenyl>carbonyl>-p-toluenesulfonamide

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