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

Base Information

Chemical Name:(-)-methyl (1R,2R,3S,5S)-1-propyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS No.:1243634-78-7
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

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

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

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

There total 11 articles about (-)-methyl (1R,2R,3S,5S)-1-propyl-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: 92.0%

: 1243634-77-6
(+)-methyl (1R,2R,3S,5S)-1-propyl-3-(hydroxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate methanesulfonic acid salt

: 98-88-4
benzoyl chloride

: 1243634-78-7
(-)-methyl (1R,2R,3S,5S)-1-propyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

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

Reference yield:

: 105-21-5
4-propylbutanolide

: 1243634-78-7
(-)-methyl (1R,2R,3S,5S)-1-propyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.33 h / -20 - -15 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 0 °C / Reflux; Inert atmosphere

3.1: toluene-4-sulfonic acid / benzene / 12 h / Reflux

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.1: titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

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

6.2: 2 h / -78 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

8.2: 20 °C / Inert atmosphere

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

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

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

12.1: benzene / 48 h / Inert atmosphere; Reflux

13.1: 5%-palladium/activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

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

With pyridine; hydrogenchloride; titanium(IV) tetraethanolate; lithium aluminium tetrahydride; 5%-palladium/activated carbon; hydrogen; isopropylmagnesium chloride; sodium hexamethyldisilazane; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); diisobutylaluminium hydride; aluminum tri-tert-butoxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; benzene;
DOI:10.1021/jo202652f

Reference yield:

: 1360562-59-9
4-hydroxy-N-methoxy-N-methylheptanamide

: 1243634-78-7
(-)-methyl (1R,2R,3S,5S)-1-propyl-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 0 °C / Reflux; Inert atmosphere

2.1: toluene-4-sulfonic acid / benzene / 12 h / Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.1: titanium(IV) tetraethanolate / dichloromethane / 20 °C / Inert atmosphere

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

5.2: 2 h / -78 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

7.2: 20 °C / Inert atmosphere

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

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

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

11.1: benzene / 48 h / Inert atmosphere; Reflux

12.1: 5%-palladium/activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

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

With pyridine; hydrogenchloride; titanium(IV) tetraethanolate; lithium aluminium tetrahydride; 5%-palladium/activated carbon; hydrogen; sodium hexamethyldisilazane; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); diisobutylaluminium hydride; aluminum tri-tert-butoxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; benzene;
DOI:10.1021/jo202652f