(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

Base Information

Chemical Name:(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester
CAS No.:1283098-14-5
Molecular Formula:C₂₁H₂₇NO₆
Molecular Weight:389.448
Hs Code.:

Synonyms:(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

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Chemical Property of (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

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Technology Process of (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

There total 8 articles about (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester 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: 96.0%

: 148533-48-6
(1R,2R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

: 98-88-4
benzoyl chloride

: 1283098-14-5
(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo200069m

Reference yield:

: 1283098-16-7
(7aR,10R,12S)-7a,8,9,10-tetrahydro-10-ethynyl-12-phenyl-12H-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine

: 1283098-14-5
(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Lindlar's catalyst; hydrogen / tetrahydrofuran / 0.17 h / 20 °C / 760.05 Torr

2.1: diethyl ether / 1 h / -40 °C

3.1: sodium hydroxide / tetrahydrofuran; methanol; water / 1 h / 60 °C

3.2: 0.5 h / 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Inert atmosphere; Reflux

5.1: sodium hydrogencarbonate / ethyl acetate / 40 h / 10 °C

6.1: methanol / 8 h / Reflux

7.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C / 760.05 Torr

8.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; Lindlar's catalyst; hydrogen; boric acid; sodium hydrogencarbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo200069m

Reference yield:

: 1042368-49-9
(2S,5R)-2-allyl-5-vinylpyrrolidine-1-carboxylic acid tert-butyl ester

: 1283098-14-5
(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Inert atmosphere; Reflux

2: sodium hydrogencarbonate / ethyl acetate / 40 h / 10 °C

3: methanol / 8 h / Reflux

4: hydrogen; boric acid / methanol; water / 3 h / 20 °C / 760.05 Torr

5: dmap; triethylamine / dichloromethane / 12 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; hydrogen; boric acid; sodium hydrogencarbonate; triethylamine; In methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo200069m