tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

Base Information

Chemical Name:tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate
CAS No.:1070764-15-6
Molecular Formula:C₂₀H₂₉NO₃
Molecular Weight:331.455
Hs Code.:

Synonyms:tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

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Chemical Property of tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

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Technology Process of tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

There total 10 articles about tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate 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:

: (3aR,4R,5S,7aS)-4-(o-tolyl)octahydro-1H-isoindol-5-ol

: 24424-99-5
di-tert-butyl dicarbonate

: 1070764-15-6
tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

Guidance literature:: In dichloromethane; at 20 ℃;
DOI:10.1021/jm400751p

Reference yield:

: 918417-38-6
diethyl (1S,2S,3R,4S)-4-hydroxy-3-(2-methylphenyl)cyclohexane-1,2-dicarboxylate

: 1070764-15-6
tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: lithium borohydride / tetrahydrofuran / 12 h / 0 - 75 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane; acetonitrile / 41 h / 20 °C

3: ethanol / 3 h / 140 °C / Sealed tube

4: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h / 20 °C / 2585.81 Torr

5: dichloromethane / 20 °C

With 2,6-dimethylpyridine; lithium borohydride; 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jm400751p

Reference yield:

: diethyl (1SR,2SR,3RS,4SR)-3-(2-methylphenyl)-4-hydroxycyclohexane-1,2-dicarboxylate

: 1070764-15-6
tert-butyl (3aR,4R,5S,7aS)-5-hydroxy-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: CHIRACEL AD column / hexane; isopropyl alcohol / Resolution of racemate

2: lithium borohydride / tetrahydrofuran / 12 h / 0 - 75 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane; acetonitrile / 41 h / 20 °C

4: ethanol / 3 h / 140 °C / Sealed tube

5: 10 wt% Pd(OH)2 on carbon; hydrogen / ethanol / 16 h / 20 °C / 2585.81 Torr

6: dichloromethane / 20 °C

With 2,6-dimethylpyridine; lithium borohydride; 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; ethanol; hexane; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1021/jm400751p