benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

Base Information

Chemical Name:benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate
CAS No.:1265966-55-9
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

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Chemical Property of benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

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Technology Process of benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

There total 9 articles about benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate 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: 94.0%

: 1265966-54-8
benzyl-(1S,5S)-7-oxo-2-azabicyclo[3.2.2]nonane-2-carboxylate

: 149-73-5
trimethyl orthoformate

: 1265966-55-9
benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

Guidance literature:: benzyl-(1S,5S)-7-oxo-2-azabicyclo[3.2.2]nonane-2-carboxylate; With toluene-4-sulfonic acid; In methanol; dichloromethane; water; at 20 ℃; for 1h; Inert atmosphere;

trimethyl orthoformate; In methanol; dichloromethane; water; at 60 ℃; Inert atmosphere;
DOI:10.1021/jo102475s

Reference yield:

: 1265966-48-0
(1R,4S)-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-one

: 1265966-55-9
benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydroxylamine hydrochloride; sodium acetate / methanol / 4 h / Reflux

2.1: pyridine; sulfuric acid; p-toluenesulfonyl chloride / 0 - 55 °C

2.2: -10 - 0 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 20 - 45 °C / Inert atmosphere

4.1: potassium carbonate / acetonitrile / 20 °C / Inert atmosphere

5.1: formic acid / water / 1 h / 20 °C

6.1: toluene-4-sulfonic acid / methanol; dichloromethane; water / 1 h / 20 °C / Inert atmosphere

6.2: 60 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; formic acid; sulfuric acid; hydroxylamine hydrochloride; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 2.1: Beckmann rearrangement / 2.2: Beckmann rearrangement;
DOI:10.1021/jo102475s

Reference yield:

: (1R,4S)-(6E)-N-hydroxy-6H-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-imine

: 1265966-55-9
benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine; sulfuric acid; p-toluenesulfonyl chloride / 0 - 55 °C

1.2: -10 - 0 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 20 - 45 °C / Inert atmosphere

3.1: potassium carbonate / acetonitrile / 20 °C / Inert atmosphere

4.1: formic acid / water / 1 h / 20 °C

5.1: toluene-4-sulfonic acid / methanol; dichloromethane; water / 1 h / 20 °C / Inert atmosphere

5.2: 60 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; formic acid; sulfuric acid; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1.1: Beckmann rearrangement / 1.2: Beckmann rearrangement;
DOI:10.1021/jo102475s