(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

Base Information

Chemical Name:(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one
CAS No.:275364-83-5
Molecular Formula:C₁₉H₂₇NO₅S
Molecular Weight:381.493
Hs Code.:

Synonyms:(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

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Chemical Property of (3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

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Technology Process of (3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

There total 2 articles about (3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one 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: 97.0%

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

: 149-73-5
trimethyl orthoformate

: 275364-83-5
(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 70 ℃; for 2h;
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

: 275364-83-5
(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / CuI; BF₃*Et₂O / tetrahydrofuran / -78 °C

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

With copper(l) iodide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1: Addition / 2: Etherification;
DOI:10.1021/ol005750s

Reference yield:

: 275364-83-5
(3aR,4R,6aR)-4-isopropyl-6,6-dimethoxy-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrol-2-one

: 275364-92-6
(1R,4S,12S,13R,14S)-4-benzenesulfonyl-13-isopropyl-2-(toluene-4-sulfonyl)-2-azatricyclo[10.2.1.1^3,4]hexadeca-3⁽¹⁶⁾,9-dien-15-one

Guidance literature:: Multi-step reaction with 10 steps

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

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

2.1: 71 percent / triphenylarsine; lithium chloride; triethylamine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 1 h / 50 °C / 15201 Torr

3.1: 78 percent / diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

4.1: 96 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 1 h / 0 °C

5.1: 95 percent / hexamethylphosphoramide / dimethylformamide / 2 h / 45 °C

6.1: n-BuLi; hexamethylphosphoramide / tetrahydrofuran; various solvent(s) / -78 °C

6.2: 65 percent / tetrahydrofuran / 2 h / -78 - -40 °C

7.1: 99 percent / aq. HCl / acetone / 4 h / 50 °C

8.1: 92 percent / copper(II) bromide / ethyl acetate / 2 h / 50 °C

9.1: 52 percent / 2,2'-azobisisobutyronitrile / toluene / 3 h / 100 °C

10.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 16 h / 40 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; copper(ll) bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Addition / 1.2: Substitution / 2.1: Carbonylation / 3.1: Reduction / 4.1: Iodination / 5.1: Substitution / 6.1: Metallation / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: Bromination / 9.1: Alkylation / 10.1: ring-closing metathesis;
DOI:10.1021/ol005750s