benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

Base Information

Chemical Name:benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate
CAS No.:1265966-53-7
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

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Chemical Property of benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

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Technology Process of benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

There total 6 articles about benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-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: 90.0%

: 1265966-52-6
(1S,5S)-spiro[4-azabicyclo[3.2.2]nonane-6,6'-[1,3]dioxolane]

: 501-53-1,94274-21-2
benzyl chloroformate

: 1265966-53-7
benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

Guidance literature:: With potassium carbonate; In acetonitrile; at 20 ℃; 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

: 1265966-53-7
benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 1265966-47-9
(1R,4S,6S)-6-hydroxy-spiro[bicyclo[2.2.2]octane-2,2'-[1,3]dioxolane]

: 1265966-53-7
benzyl-(1S,5S)-4H-spiro[4-azabicyclo[3.2.2]nonane-6,2'-[1,3]dioxolane]-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

3.2: -10 - 0 °C

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

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

With pyridine; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; sulfuric acid; hydroxylamine hydrochloride; sodium acetate; potassium carbonate; 4-methylmorpholine N-oxide; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; acetonitrile; 3.1: Beckmann rearrangement / 3.2: Beckmann rearrangement;
DOI:10.1021/jo102475s