(3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole

Base Information

• Chemical Name: (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole
• CAS No.: 111923-09-2
• Molecular Formula: C₂₂H₂₃NO₃
• Molecular Weight: 349.43
• Mol file: 111923-09-2.mol

Synonyms:(3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole

Chemical Property of (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole

There total 4 articles about (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole 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: 47.0%

(3aS*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,6,7,7a-hexahydro-1H-indol-6-one (111923-07-0) → (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole (111923-09-2) + (3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole (111923-08-1)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo00249a011

Reference yield:

4-<2-<<(allyloxy)carbonyl>benzylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (111923-06-9) → (3aS,7aR)-3a-Benzo[1,3]dioxol-5-yl-1-benzyl-2,3,3a,6,7,7a-hexahydro-1H-indol-6-ol (111923-08-1,111923-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Ph₃P, Bu(Et)CHCO₂H / Pd(Ph₃P)4 / CH₂Cl₂ / 48 h / Ambient temperature

2: AlH₃ / tetrahydrofuran

With aluminium hydride; 2-Ethylhexanoic acid; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)95766-6

Reference yield:

4-<2-<<(allyloxy)carbonyl>benzylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (111923-06-9) → (3aS*,6S*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole (111923-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / 2-ethylhexanoic acid, Pd(PPh₃)4, Ph₃P / CH₂Cl₂ / 24 h / Ambient temperature

2: 31 percent / AlH₃ / tetrahydrofuran / 2 h / 0 °C

With aluminium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00249a011

upstream raw materials:

(3aS*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,6,7,7a-hexahydro-1H-indol-6-one

4-<2-<<(allyloxy)carbonyl>benzylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone

Downstream raw materials:

(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-methoxy-2,3,3a,6,7,7a-hexahydro-1H-indole

(3aS*,4R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-4-methoxy-2,3,3a,4,7,7a-hexahydro-1H-indole

(+/-)-buphanisine

(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole