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

Base Information

Chemical Name:(-)-methyl (1R,2R,3S,5S)-3-(benzoyloxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS No.:1243634-58-3
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

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

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

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

There total 23 articles about (-)-methyl (1R,2R,3S,5S)-3-(benzoyloxy)-1,8-dimethyl-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: 94.0%

: 1243634-57-2
(-)-methyl (1R,2R,3S,5S)-3-(hydroxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate methanesulfonic acid salt

: 98-88-4
benzoyl chloride

: 1243634-58-3
(-)-methyl (1R,2R,3S,5S)-3-(benzoyloxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: With pyridine; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1021/ol1017118

Reference yield:

: 29021-98-5
3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol

: 1243634-58-3
(-)-methyl (1R,2R,3S,5S)-3-(benzoyloxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

1.2: 1.25 h / -78 - 20 °C / Inert atmosphere

2.1: dichloromethane / 17 h / 20 °C

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere

4.1: manganese(IV) oxide / dichloromethane / 24 h

5.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine / chloroform / 41 h / 4 °C

6.1: chloroform / 2 h / 20 °C

7.1: triethylsilane; triethylamine; palladium dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

8.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C

9.1: aluminum tri-tert-butoxide / toluene / 68 h / 20 - 150 °C / pressure tube

10.1: benzene / 24 h / 85 °C

11.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 2585.81 - 3620.13 Torr

12.1: dmap; triethylamine / dichloromethane / 17 h / 0 - 20 °C

With hydrogenchloride; triethylsilane; dmap; manganese(IV) oxide; oxalyl dichloride; (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; palladium 10% on activated carbon; water; hydrogen; diisobutylaluminium hydride; aluminum tri-tert-butoxide; dimethyl sulfoxide; triethylamine; palladium dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; toluene; benzene; 2.1: Wittig reaction / 5.1: Michael condensation / 6.1: Wittig reaction / 10.1: sealed pressure tube;
DOI:10.1002/adsc.201100917

Reference yield:

: 1243634-48-1
(S,E)-2-(4-methoxy-4-oxobut-2-en-1-yl)-5-methyl-3,4-dihydro-2H-pyrrole 1-oxide.

: 1243634-58-3
(-)-methyl (1R,2R,3S,5S)-3-(benzoyloxy)-1,8-dimethyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: aluminum tri-tert-butoxide / toluene / 102 h / 20 - 110 °C / Reflux

2: benzene / 24 h / Inert atmosphere; Reflux

3: 5%-palladium/activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

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

With pyridine; 5%-palladium/activated carbon; hydrogen; aluminum tri-tert-butoxide; In methanol; toluene; benzene;
DOI:10.1021/jo202652f