rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol

Base Information

• Chemical Name: rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol
• CAS No.: 82769-20-8
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• DSSTox Substance ID: DTXSID601147647
• Mol file: 82769-20-8.mol

Synonyms:DTXSID601147647;rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol;82769-20-8

Chemical Property of rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 291.18344366
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CCC2(C1CC(CC2)O)C3=CC(=C(C=C3)OC)OC
• Isomeric SMILES: CN1CC[C@@]2([C@H]1C[C@@H](CC2)O)C3=CC(=C(C=C3)OC)OC

Technology Process of rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol

There total 26 articles about rel-(3aR,6R,7aR)-3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-1H-indol-6-ol 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: 96.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 6-hydroxy-3a-[3,4-(dimethoxy)phenyl]-2,3,3a,4,5,6,7,7a-octahydroindole → (+/-)-6-epimesembranol (82769-20-8)

Guidance literature:

With sodium cyanoborohydride; zinc(II) chloride; In methanol; water; at 20 ℃; for 0.0833333h;

DOI:10.1021/ol0346685

Reference yield: 68.0%

mesembrine (6023-73-0) → (+/-)-6-epimesembranol (82769-20-8) + (+/-)-mesembranol (82769-19-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h; Heating;

DOI:10.1021/jo00001a021

Reference yield:

4-(benzyloxy)cyclohexanone (2987-06-6) → (+/-)-6-epimesembranol (82769-20-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-butyllithium / 1.) THF, -78 deg C, 2.) -78 deg C, 2 h

2: p-toluenesulfonic acid / acetone / 48 h / Ambient temperature

3: Zn / diethyl ether / 3 h

4: Zn, NH₄Cl / methanol / 16 h / Heating

5: molecular sieves 3A, pyridine / 24 h / 25 °C

6: 1.) p-toluenesulfonyl chloride, 2.) H₂O / 1.) pyridine, RT, 6 h, 2.) RT, 46 h

7: 74.5 percent / BH₃*THF / tetrahydrofuran / 1 h / Heating

8: 35 mg / H₂, conc. HCl / 5percent Pd/C / ethanol / 3 h / 3102.9 Torr

With pyridine; hydrogenchloride; n-butyllithium; borane-THF; 3 A molecular sieve; water; hydrogen; ammonium chloride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; acetone;

DOI:10.1021/jo00141a015

upstream raw materials:

mesembrine

(3aR,7aR)-3a-(3,4-Dimethoxy-phenyl)-6-hydroxy-1-methyl-octahydro-indol-2-one

1-methyl-3a-(3,4-dimethoxyphenyl)-6-(benzyloxy)-cis-octahydroindole

formaldehyd

Downstream raw materials:

mesembrine

Refernces

• 1、 Ishibashi, Hiroyuki,So, Taru Su,Okochi, Kyoko,Sato, Tatsunori,Nakamura, Nobuyuki,et al.. "Radical Cyclization of N-(Cyclohex-2-enyl)-α,α-dichloroacetamides. Stereoselective Syntheses of (+/-)-Mesembranol and (+/-)-Elwesine". . p. 95 - 102. Retrieved 2007/10/02.
• 2、 Jeffs, Peter W.,Cortese, Nicholas A.,Wolfram, Joachim. "Synthesis of (+/-)-Mesembranol and (+/-)-O-Methyljoubertiamine. Aza-Ring Expansion of cis-Bicyclooctanones". . p. 3881 - 3886. Retrieved 2007/10/02.