methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Base Information

Chemical Name:methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS No.:1355075-42-1
Molecular Formula:C₂₃H₂₅NO₄
Molecular Weight:379.456
Hs Code.:

Synonyms:

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Chemical Property of methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Chemical Property:

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Technology Process of methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

There total 15 articles about methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-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: 80.0%

: 1355075-42-1
methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:

Reference yield:

: 50880-21-2
3-(2-phenyl-1,3-dioxolan-2-yl)propanal

: 1355075-42-1
methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: titanium(IV) tetraethanolate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 0.17 h / -78 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; methanol; water / 16 h / 20 °C

6.1: urea hydrogen peroxide adduct; methyltrioxorhenium(VII) / methanol / 15 h / 20 °C / Inert atmosphere

7.1: aluminum tri-tert-butoxide / toluene / 72 h / 110 °C

8.1: benzene / 72 h / Inert atmosphere; Reflux

9.1: 5%-palladium/activated carbon; hydrogen / methanol / 10 h / 20 °C / 760.05 Torr

10.1: pyridine / 20 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; titanium(IV) tetraethanolate; 5%-palladium/activated carbon; hydrogen; sodium hexamethyldisilazane; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); diisobutylaluminium hydride; aluminum tri-tert-butoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; water; toluene; acetonitrile; benzene;
DOI:10.1021/jo202652f

Reference yield:

: 1355075-58-9
(Ss,3S)-(+)-methyl N-(tert-butylsulfinyl)-3-amino-5-(2-phenyl-1,3-dioxolan-2-yl)pentanoate

: 1355075-42-1
methyl (1R,2R,3S,5S)-(-)-1-phenyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / toluene / 0.17 h / -78 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; methanol; water / 16 h / 20 °C

4.1: urea hydrogen peroxide adduct; methyltrioxorhenium(VII) / methanol / 15 h / 20 °C / Inert atmosphere

5.1: aluminum tri-tert-butoxide / toluene / 72 h / 110 °C

6.1: benzene / 72 h / Inert atmosphere; Reflux

7.1: 5%-palladium/activated carbon; hydrogen / methanol / 10 h / 20 °C / 760.05 Torr

8.1: pyridine / 20 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; 5%-palladium/activated carbon; hydrogen; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); diisobutylaluminium hydride; aluminum tri-tert-butoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; water; toluene; acetonitrile; benzene;
DOI:10.1021/jo202652f