(+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole

Base Information

• Chemical Name: (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole
• CAS No.: 135283-62-4
• Molecular Formula: C₂₂H₂₃NO₃
• Molecular Weight: 349.43
• Mol file: 135283-62-4.mol

Synonyms:(+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole

Chemical Property of (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole

There total 16 articles about (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole 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: 97.0%

(+/-)-cis-2-N-Benzyl-6a<(E)-2-(1,3-benzodioxol-5-yl)ethenyl>-1-oxa-3-azabicyclo<3.3.0>octane (135191-29-6) → (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole (135283-62-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; -20 deg C -> 23 deg C;

DOI:10.1021/jo00017a002

Reference yield:

(+/-)-cis-2-(N-Benzylamino)-1-<2-(1,3-benzodioxol-5-yl)ethynyl>cyclopentanol (135191-27-4) → (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole (135283-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / LiAlH₄ / diethyl ether / 4 h / Heating

2: 81 percent / Na₂SO₄, camphorsulfonic acid / H₂O; CH₂Cl₂ / 8 h / 23 °C

3: 97 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.) -20 deg C, 30 min, 2.) 23 deg C, 15 min

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium sulfate; In diethyl ether; dichloromethane; water;

DOI:10.1021/jo00069a032

Reference yield:

(+/-)-cis-2-(N-Benzylamino)-1-<(E)-2-(1,3-benzodioxol-5-yl)ethenyl>cyclopentanol (135191-28-5) → (+/-)-(3R*,3aS*,7aS*)-N-Benzyl-3-(1,3-benzodioxol-5-yl)-4-oxooctahydroindole (135283-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Na₂SO₄, camphorsulfonic acid / H₂O; CH₂Cl₂ / 8 h / 23 °C

2: 97 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.) -20 deg C, 30 min, 2.) 23 deg C, 15 min

With camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium sulfate; In dichloromethane; water;

DOI:10.1021/jo00069a032

upstream raw materials:

(+/-)-cis-2-N-Benzyl-6a<(E)-2-(1,3-benzodioxol-5-yl)ethenyl>-1-oxa-3-azabicyclo<3.3.0>octane

3,4-methylenedioxyphenylethyne

piperonal

(+/-)-trans-2-bromocyclopentanol

Downstream raw materials:

(+/-)-pancracine