(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester
CAS No.:275364-84-6
Molecular Formula:C₂₁H₂₉NO₆S
Molecular Weight:423.53
Hs Code.:

Synonyms:(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

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Chemical Property of (3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

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Technology Process of (3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

There total 4 articles about (3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid 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: 71.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 275364-81-3
Trifluoro-methanesulfonic acid (3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-yl ester

: 275364-84-6
(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

Guidance literature:: With triphenyl-arsane; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In acetonitrile; at 50 ℃; for 1h; under 15201 Torr;
DOI:10.1021/ol005750s

Reference yield:

: 201014-33-7
(3aR,6aR)-1-(Toluene-4-sulfonyl)-1,3,3a,6a-tetrahydro-cyclopenta[b]pyrrole-2,6-dione

: 275364-84-6
(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / CuI; BF₃*Et₂O / tetrahydrofuran / -78 °C

2.1: 97 percent / p-toluenesulfonic acid / methanol / 2 h / 70 °C

3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: hexamethylphosphoramide / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

4.1: 71 percent / triphenylarsine; lithium chloride; triethylamine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 1 h / 50 °C / 15201 Torr

With copper(l) iodide; triphenyl-arsane; boron trifluoride diethyl etherate; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol; toluene; acetonitrile; 1.1: Addition / 2.1: Etherification / 3.1: Addition / 3.2: Substitution / 4.1: Carbonylation;
DOI:10.1021/ol005750s

Reference yield:

: 201014-29-1
(3aR,4R,6aR)-4-Isopropyl-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrole-2,6-dione

: 275364-84-6
(3aS,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / p-toluenesulfonic acid / methanol / 2 h / 70 °C

2.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: hexamethylphosphoramide / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

3.1: 71 percent / triphenylarsine; lithium chloride; triethylamine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 1 h / 50 °C / 15201 Torr

With triphenyl-arsane; potassium hexamethylsilazane; toluene-4-sulfonic acid; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol; toluene; acetonitrile; 1.1: Etherification / 2.1: Addition / 2.2: Substitution / 3.1: Carbonylation;
DOI:10.1021/ol005750s