(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

Base Information

Chemical Name:(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione
CAS No.:467229-82-9
Molecular Formula:C₁₅H₁₇N₅O₂
Molecular Weight:299.332
Hs Code.:

Synonyms:(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

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Chemical Property of (1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

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Technology Process of (1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

There total 5 articles about (1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione 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: 79.0%

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

: 467229-82-9
(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; for 2h; Heating;
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

: 467229-82-9
(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

Guidance literature:: Multi-step reaction with 5 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

5: 79 percent / sodium azide / dimethylformamide / 2 h / Heating

With sodium tetrahydroborate; sodium azide; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; 1: Dieckmann cyclization;
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

: 467229-82-9
(1S,2S,5S)-2-azido-6-benzyl-8-methyl-6,8-diazabicyclo[3.2.2]nonane-7,9-dione

Guidance literature:: Multi-step reaction with 3 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

3: 79 percent / sodium azide / dimethylformamide / 2 h / Heating

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