4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Base Information

• Chemical Name: 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline
• CAS No.: 58637-23-3
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.365
• Mol file: 58637-23-3.mol

Synonyms:

Chemical Property of 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline

There total 9 articles about 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline 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:

N-ethyl-4-piperidone (3612-18-8) → 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline (58637-23-3,58637-24-4,70390-78-2,70390-80-6,70745-59-4,102538-23-8,111765-98-1,111765-99-2,58414-83-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-butyllithium / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 2 h

2: 90 percent / 85percent aq. phosphoric acid / 3 h / 70 - 80 °C

3: 1.) n-butyllithium / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, ether, -50 deg C

4: sodium iodide, K₂CO₃ / acetonitrile / 20 h / Heating

5: 93 percent / H₂ / platinum oxide / ethanol / 16 h / 3102.9 Torr / Ambient temperature

6: 4.9 g / 1,2-dichloro-ethane / 2 h / Heating

7: HCl / ethanol / 1 h / Heating

With hydrogenchloride; n-butyllithium; phosphoric acid; hydrogen; potassium carbonate; sodium iodide; platinum(IV) oxide; In ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00158a033

Reference yield:

3-methoxyphenyl bromide (2398-37-0) → 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline (58637-23-3,58637-24-4,70390-78-2,70390-80-6,70745-59-4,102538-23-8,111765-98-1,111765-99-2,58414-83-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-butyllithium / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 2 h

2: 90 percent / 85percent aq. phosphoric acid / 3 h / 70 - 80 °C

3: 1.) n-butyllithium / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, ether, -50 deg C

4: sodium iodide, K₂CO₃ / acetonitrile / 20 h / Heating

5: 93 percent / H₂ / platinum oxide / ethanol / 16 h / 3102.9 Torr / Ambient temperature

6: 4.9 g / 1,2-dichloro-ethane / 2 h / Heating

7: HCl / ethanol / 1 h / Heating

With hydrogenchloride; n-butyllithium; phosphoric acid; hydrogen; potassium carbonate; sodium iodide; platinum(IV) oxide; In ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00158a033

Reference yield:

1,2,3,6-tetrahydro-4-(3-methoxyphenyl)-N-ethylpyridine (102538-16-9) → 4a-(3-methoxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline (58637-23-3,58637-24-4,70390-78-2,70390-80-6,70745-59-4,102538-23-8,111765-98-1,111765-99-2,58414-83-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, ether, -50 deg C

2: sodium iodide, K₂CO₃ / acetonitrile / 20 h / Heating

3: 93 percent / H₂ / platinum oxide / ethanol / 16 h / 3102.9 Torr / Ambient temperature

4: 4.9 g / 1,2-dichloro-ethane / 2 h / Heating

5: HCl / ethanol / 1 h / Heating

With hydrogenchloride; n-butyllithium; hydrogen; potassium carbonate; sodium iodide; platinum(IV) oxide; In ethanol; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1021/jm00158a033

upstream raw materials:

(4aS,8aS)-4a-(3-Methoxy-phenyl)-octahydro-isoquinoline-2-carboxylic acid vinyl ester

N-ethyl-4-piperidone

3-methoxyphenyl bromide

1,2,3,6-tetrahydro-4-(3-methoxyphenyl)-N-ethylpyridine

Downstream raw materials:

3-<2-(phenylmethyl)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-isoquinolinyl>phenol

3-<2-(cyclobutylmethyl)-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-isoquinolinyl>phenol

3-(2-allyl-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-isoquinolinyl)phenol

3-(2-n-propyl-1,2,3,4,4a,5,6,7,8,8aα-decahydro-4aβ-isoquinolinyl)phenol