Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester
CAS No.:292615-27-1
Molecular Formula:C₂₁H₃₃NO₃S
Molecular Weight:379.564
Hs Code.:

Synonyms:Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

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Technology Process of Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

There total 12 articles about Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl 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:

: [(R)-5-Butyl-1-(2-trimethylsilanyl-ethanesulfonyl)-pyrrolidin-2-yl]-acetic acid benzyl ester

: 292615-27-1
Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: H₂ / Pd/C / methanol / 12 h / 20 °C

2.1: (COCl)2 / CH₂Cl₂

2.2: diethyl ether; CH₂Cl₂

2.3: Ag₂O / diethyl ether; CH₂Cl₂ / 1 h / 50 °C

3.1: LAH / diethyl ether / 1 h / 0 °C

4.1: CsF / dimethylformamide / 18 h / 95 °C

5.1: CH₂Cl₂ / 1 h / 0 °C

6.1: TEA / CH₂Cl₂ / 2 h / 0 °C

7.1: NaBH₄ / ethanol / 2 h / 20 °C

8.1: TMSI / acetonitrile / 1 h / 20 °C

9.1: K₂CO₃ / acetonitrile / 2 h / 20 °C

10.1: 58 percent / Bu₃SnH; AIBN / benzene / 7 h / Heating

11.1: LAH / tetrahydrofuran / 1 h / 0 °C

12.1: TEA / CH₂Cl₂ / 2 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); trimethylsilyl iodide; TEA; hydrogen; tri-n-butyl-tin hydride; potassium carbonate; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Hydrogenation / 2.1: Chlorination / 2.2: Substitution / 2.3: Rearrangement / 3.1: Reduction / 4.1: sulfonamide cleavage / 5.1: t-butoxycarbonylation / 6.1: Tosylation / 7.1: Substitution / 8.1: carbamate cleavage / 9.1: Addition / 10.1: Cyclization / 11.1: Reduction / 12.1: Tosylation;
DOI:10.1021/ol006094z

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 2-((3R,5S,8aR)-3-Butyl-octahydro-indolizin-5-yl)-ethanol

: 292615-27-1
Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

Guidance literature:: With TEA; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol006094z

Reference yield:

: 3-((R)-5-Butyl-pyrrolidin-2-yl)-propan-1-ol

: 292615-27-1
Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: CH₂Cl₂ / 1 h / 0 °C

2: TEA / CH₂Cl₂ / 2 h / 0 °C

3: NaBH₄ / ethanol / 2 h / 20 °C

4: TMSI / acetonitrile / 1 h / 20 °C

5: K₂CO₃ / acetonitrile / 2 h / 20 °C

6: 58 percent / Bu₃SnH; AIBN / benzene / 7 h / Heating

7: LAH / tetrahydrofuran / 1 h / 0 °C

8: TEA / CH₂Cl₂ / 2 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); trimethylsilyl iodide; TEA; tri-n-butyl-tin hydride; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene; 1: t-butoxycarbonylation / 2: Tosylation / 3: Substitution / 4: carbamate cleavage / 5: Addition / 6: Cyclization / 7: Reduction / 8: Tosylation;
DOI:10.1021/ol006094z