6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

Base Information

Chemical Name:6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate
CAS No.:1374411-79-6
Molecular Formula:C₂₇H₃₅NO₄
Molecular Weight:437.579
Hs Code.:

Synonyms:6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

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Chemical Property of 6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

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Technology Process of 6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

There total 3 articles about 6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate 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: 79.0%

: 1374411-70-7
5-methyl 2-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] pyridine-2,5-dicarboxylate

: 109-64-8
1,3-dibromo-propane

: 1374411-79-6
6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

Guidance literature:: 5-methyl 2-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] pyridine-2,5-dicarboxylate; With lithium trimethylstannyl; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

1,3-dibromo-propane; In tetrahydrofuran; at -78 - 20 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/ejoc.201101427

Reference yield:

: 17874-79-2
pyridine-2,5-dicarboxylic acid 5-methyl ester

: 1374411-79-6
6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 168 h / Reflux; Inert atmosphere

2.1: lithium trimethylstannyl / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 12 h / -78 - 20 °C / Inert atmosphere

With dmap; lithium trimethylstannyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201101427

Reference yield:

: 65253-04-5
(-)-8-phenylmenthol

: 1374411-79-6
6-methyl 8a-[(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (8aR)-1,2,3,8a-tetrahydroindolizine-6,8a-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 168 h / Reflux; Inert atmosphere

2.1: lithium trimethylstannyl / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 12 h / -78 - 20 °C / Inert atmosphere

With dmap; lithium trimethylstannyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201101427