(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

Base Information

Chemical Name:(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone
CAS No.:1312994-84-5
Molecular Formula:C₁₆H₂₃NO₂
Molecular Weight:261.364
Hs Code.:

Synonyms:(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

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Chemical Property of (5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

Chemical Property:

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Technology Process of (5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

There total 9 articles about (5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone 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:

: 7214-50-8
5-methylcyclohex-2-en-1-one

: 1220796-71-3
(S)-1,2,3,5,6,8a-hexahydroindolizine-8-carbaldehyde

: 1312994-83-4
(5R)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

: 1312994-84-5
(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

Guidance literature:: 5-methylcyclohex-2-en-1-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

(S)-1,2,3,5,6,8a-hexahydroindolizine-8-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 2h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol2014939

Reference yield:

: 1312994-79-8
(S)-1-(3,3-diethoxypropyl)-2-(ethylthioethynyl)pyrrolidine

: 1312994-83-4
(5R)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

: 1312994-84-5
(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 steps

1.1: formic acid / 2 h / 100 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate; triethylamine / dichloromethane / 18 h / 45 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

5.2: 2 h / -78 °C / Inert atmosphere

With n-butyllithium; formic acid; oxalyl dichloride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol2014939

Reference yield:

: 1312994-81-2
(S)-S-ethyl 1,2,3,5,6,8a-hexahydroindolizine-8-carbothioate

: 1312994-83-4
(5R)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

: 1312994-84-5
(5S)-6-(((S)-1,2,3,5,6,8a-hexahydroindolizin-8-yl)(hydroxy)methyl)-5-methylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1.1: silver trifluoromethanesulfonate; triethylamine / dichloromethane / 18 h / 45 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol2014939