(3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole

Base Information

• Chemical Name: (3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole
• CAS No.: 318502-89-5
• Molecular Formula: C₁₃H₂₃NO₃
• Molecular Weight: 241.331
• Mol file: 318502-89-5.mol

Synonyms:(3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole;(3aR,7aS)-rel-tert-Butyl 5-hydroxyhexahydro-1H-isoindole-2(3H)-carboxylate

Chemical Property of (3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(3AR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole 97.0% ^*data from reagent suppliers

Safty Information:

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Technology Process of (3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole

There total 8 articles about (3aR,7aS)-rel-2-Boc-5-hydroxy-octahydro-2H-Isoindole 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: 94.2%

3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)carboxylic acid tert-butyl ester → tert-butyl 5-hydroxyhexahydro-1H-isoindole-2(3H)-carboxylate (203661-67-0,318502-89-5,2007919-65-3)

Guidance literature:

3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)carboxylic acid tert-butyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 60 ℃; for 1.5h;

Reference yield:

1,2,3,6-tertahydrophthalimide (85-40-5) → tert-butyl 5-hydroxyhexahydro-1H-isoindole-2(3H)-carboxylate (203661-67-0,318502-89-5,2007919-65-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 21 h / 60 °C

2.1: dichloromethane / 21.5 h / 0 - 20 °C

3.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: 1.5 h / 60 °C

With lithium aluminium tetrahydride; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;

Reference yield:

2,3,3a,4,7,7a-hexahydro-1H-isoindole (10533-30-9) → tert-butyl 5-hydroxyhexahydro-1H-isoindole-2(3H)-carboxylate (203661-67-0,318502-89-5,2007919-65-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 21.5 h / 0 - 20 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 1.5 h / 60 °C

With dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(3aR,7aS)-tert-butyl 3a,4,7,7a-tetrahydro-1H-isoindole-2(3H)-carboxylate

(cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole

cis-1,2,3,6-Tetrahydrophthalimide

1,2,3,6-tertahydrophthalimide

Downstream raw materials:

tert-butyl 5-oxohexahydro-1H-isoindole-2(3H)-carboxylate

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