[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

Base Information

Chemical Name:[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate
CAS No.:467229-81-8
Molecular Formula:C₁₆H₂₀N₂O₅S
Molecular Weight:352.411
Hs Code.:

Synonyms:[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

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Chemical Property of [(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

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Technology Process of [(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

There total 4 articles about [(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate 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%

: 124-63-0
methanesulfonyl chloride

: 467229-80-7
(1S,2R,5S)-6-benzyl-2-hydroxy-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

: 467229-81-8
[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1016/S0968-0896(02)00043-3

Reference yield:

: 269717-68-2
(1S,5S)-6-benzyl-2-methoxy-8-methyl-6.8-diazabicyclo[3.2.2]nonane-2,7,9-trione

: 467229-81-8
[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

Guidance literature:: Multi-step reaction with 2 steps

1: 27 percent / sodium borohydride / tetrahydrofuran; propan-2-ol; H₂O / 16 h / 20 °C

2: 92 percent / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol;
DOI:10.1016/S0968-0896(02)00043-3

Reference yield:

: 269717-63-7
methyl (S)-3-(1-benzyl-4-methyl-3,6-dioxopiperazin-2-yl)propionate

: 467229-81-8
[(1S,2R,5S)-(6-benzyl-8-methyl-7,9-dioxo-6,8-diazabicyclo[3.2.2]nonan-2-yl)]methanesulphonate

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1.5 h / -78 - 20 °C

2: 6.70 g / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 16 h / 20 °C

3: 27 percent / sodium borohydride / tetrahydrofuran; propan-2-ol; H₂O / 16 h / 20 °C

4: 92 percent / triethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; isopropyl alcohol; 1: Dieckmann cyclization;
DOI:10.1016/S0968-0896(02)00043-3