(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

Base Information

Chemical Name:(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate
CAS No.:1265966-56-0
Molecular Formula:C₁₇H₂₁NO₃
Molecular Weight:287.359
Hs Code.:

Synonyms:(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

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Chemical Property of (1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

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Technology Process of (1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

There total 12 articles about (1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-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: 92.0%

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

: 1265966-56-0
(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

Guidance literature:: benzyl-(1S,5S)-7,7-dimethoxy-2-azabicyclo[3.2.2]nonane-2-carboxylate; With iron(III) chloride; acetic anhydride; at -5 ℃; Inert atmosphere;

With sodium hydrogencarbonate; triethylamine; In ethyl acetate; at 5 - 12 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo102475s

Reference yield:

: 129100-39-6
(1R,4S,6S)-bicyclo<2.2.2>octane-6-ol-2-one

: 1265966-56-0
(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: dmap / dichloromethane / 0 - 20 °C

2.1: toluene-4-sulfonic acid / toluene / 2.5 h / Reflux

3.1: lithium hydroxide monohydrate; water / methanol / 48 h / 20 °C

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 20 °C / Inert atmosphere; Molecular sieve

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

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

6.2: -10 - 0 °C

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

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

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

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

10.2: 60 °C / Inert atmosphere

11.1: iron(III) chloride; acetic anhydride / -5 °C / Inert atmosphere

11.2: 1 h / 5 - 12 °C / Inert atmosphere

With pyridine; dmap; iron(III) chloride; lithium aluminium tetrahydride; formic acid; tetrapropylammonium perruthennate; lithium hydroxide monohydrate; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 6.1: Beckmann rearrangement / 6.2: Beckmann rearrangement;
DOI:10.1021/jo102475s

Reference yield:

: 1265966-46-8
(1R,4S,6S)-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolan]-6-yl benzoate

: 1265966-56-0
(1S,5S)-benzyl-7-methoxy-2-azabicyclo[3.2.2]non-6-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium hydroxide monohydrate; water / methanol / 48 h / 20 °C

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 20 °C / Inert atmosphere; Molecular sieve

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

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

4.2: -10 - 0 °C

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

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

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

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

8.2: 60 °C / Inert atmosphere

9.1: iron(III) chloride; acetic anhydride / -5 °C / Inert atmosphere

9.2: 1 h / 5 - 12 °C / Inert atmosphere

With pyridine; iron(III) chloride; lithium aluminium tetrahydride; formic acid; tetrapropylammonium perruthennate; lithium hydroxide monohydrate; sulfuric acid; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 4.1: Beckmann rearrangement / 4.2: Beckmann rearrangement;
DOI:10.1021/jo102475s