toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester
• CAS No.: 1202362-65-9
• Molecular Formula: C₂₄H₃₁NO₅S
• Molecular Weight: 445.58
• Mol file: 1202362-65-9.mol

Synonyms:toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester

Chemical Property of toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester

There total 14 articles about toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester 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: 73.0%

((2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-2-yl)-methanol (1202362-64-8) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester (1202362-65-9)

Guidance literature:

With pyridine; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2013.11.012

Reference yield:

5,8-dihydro-1-naphthol (27673-48-9) → toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester (1202362-65-9)

Guidance literature:

Multi-step reaction with 12 steps

1: potassium carbonate / acetone / 2.5 h / Inert atmosphere; Reflux

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

3: sodium azide; sulfuric acid / dimethyl sulfoxide / 23 h / 60 °C / Inert atmosphere

4: hydrogen; palladium 10% on activated carbon / ethanol / 1875.19 Torr / Inert atmosphere

5: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

6: Chiralpak AD 21.2×250mm column / ethanol; diethylamine / Inert atmosphere; Resolution of racemate

7: hydrogenchloride / methanol; diethyl ether / 2 h / Inert atmosphere

8: triethylamine / tetrahydrofuran / 0.33 h / Inert atmosphere

9: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 90 °C / Inert atmosphere; Microwave irradiation

10: 1,2-dichloro-ethane / 120 °C / Inert atmosphere

11: sodium hydroxide / 130 °C / Inert atmosphere

12: pyridine / 4 h / 20 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; sulfuric acid; palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; diethylamine; acetone;

DOI:10.1016/j.bmc.2013.11.012

Reference yield:

α-naphthol (90-15-3) → toluene-4-sulfonic acid (2R,4aR,10aR)-9-methoxy-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naptho[2,3-b][1,4]oxazin-2-ylmethyl ester (1202362-65-9)

Guidance literature:

Multi-step reaction with 13 steps

1: ammonia; lithium / ethanol / -78 °C / Inert atmosphere

2: potassium carbonate / acetone / 2.5 h / Inert atmosphere; Reflux

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere

4: sodium azide; sulfuric acid / dimethyl sulfoxide / 23 h / 60 °C / Inert atmosphere

5: hydrogen; palladium 10% on activated carbon / ethanol / 1875.19 Torr / Inert atmosphere

6: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

7: Chiralpak AD 21.2×250mm column / ethanol; diethylamine / Inert atmosphere; Resolution of racemate

8: hydrogenchloride / methanol; diethyl ether / 2 h / Inert atmosphere

9: triethylamine / tetrahydrofuran / 0.33 h / Inert atmosphere

10: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 90 °C / Inert atmosphere; Microwave irradiation

11: 1,2-dichloro-ethane / 120 °C / Inert atmosphere

12: sodium hydroxide / 130 °C / Inert atmosphere

13: pyridine / 4 h / 20 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; sulfuric acid; palladium 10% on activated carbon; ammonia; hydrogen; lithium; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; diethylamine; acetone; 1: |Birch Reduction;

DOI:10.1016/j.bmc.2013.11.012

upstream raw materials:

α-naphthol

5,8-dihydro-1-naphthol

1,4-dihydro-5-methoxynaphthalene

3-methoxy-1a,2,7,7a-tetrahydronaphtho[2,3-b]oxirene

Downstream raw materials:

(2R,4aR,10aR)-9-methoxy-2-(3-phenyl-pyrazol-1-ylmethyl)-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine