(2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline

Base Information

• Chemical Name: (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline
• CAS No.: 160798-33-4
• Molecular Formula: C₂₀H₃₁N
• Molecular Weight: 285.473
• Mol file: 160798-33-4.mol

Synonyms:(2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline

Chemical Property of (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline

There total 21 articles about (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline 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: 68.0%

(2S,4aS,5S,8aR)-1-Benzyl-5-methyl-2-propylspiro (160728-72-3) → (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline (160798-33-4)

Guidance literature:

With nickel; In 1,4-dioxane; Heating;

DOI:10.1016/0040-4039(94)88469-2

Reference yield: 54.0%

(2S,4aS,5RS,8aR)-1-Benzoyl-5-methyl-2-propyldecahydroquinoline → (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline (160798-33-4) + (2S,4aS,5S,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline (178740-06-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1039/P19960001113

Reference yield:

trans-Pent-2-enyl(triphenyl)phosphonium bromide (7348-72-3) → (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-propyldecahydroquinoline (160798-33-4)

Guidance literature:

Multi-step reaction with 19 steps

1: 95 percent / t-BuOK / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 5 min

2: 1.) DIBALH, 2.) I₂ / 1.) CH₂Cl₂, hexane, r.t., 1 h, 2.) benzene, irradiation, 15 min

3: 95 percent / pyridine / 4 h / 0 °C

4: 93 percent / dimethylsulfoxide / 1 h / 55 °C

5: 84 percent / 25percent aq. NaOH / methanol / 9 h / Heating

6: 88 percent / diethyl ether / 0.25 h / 0 °C

7: 89 percent / KOH, NH₂OH*HCl / methanol / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min

8: aq. Pr₄NIO₄ / methanol / 0.5 h / 0 °C

9: 100 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 0.5 h

10: 2.) NaBH₃CN / 1.) THF, 0 deg C, 1 h, 2.) 0 deg C, 30 min

11: 91 percent / Zn, 85percent aq. AcOH / 1 h / 60 °C

12: 98 percent / 10percent aq. K₂CO₃ / CH₂Cl₂ / 2 h / 0 °C

13: 99 percent / H₂ / 10percent Pd/C / methanol / 0.5 h

14: 74 percent / PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

15: 74 percent / KOH / ethanol / 0.17 h / 0 °C

16: 50 percent / aq. KHSO₄ / methanol / 48 h / Ambient temperature

17: 71 percent / H₂, aq HCl / 10percent Pd/C / methanol / 0.5 h

18: 57 percent / Zn, HCl / diethyl ether / 2 h / 0 °C

19: 28 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium hydrogensulfate; lithium aluminium tetrahydride; tetrapropylammonium periodate; 3 A molecular sieve; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; iodine; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; acetic acid; pyridinium chlorochromate; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1039/P19960001113

upstream raw materials:

(2S,4aS,5S,8aR)-1-Benzyl-5-methyl-2-propylspiro

trans-Pent-2-enyl(triphenyl)phosphonium bromide

(4E,6E,3S)-3-Benzyloxynona-4,6-dienol

(5E,7E,3S)-4-Benzyloxydeca-5,7-dienoic acid

Downstream raw materials:

(-)-pumiliotoxin C hydrochloride

(-)-pumiliotoxin C

Refernces

• 1、 Naruse, Masaichi,Aoyagi, Sakae,Kibayashi, Chihiro. "Total synthesis of (-)-pumiliotoxin C by aqueous intramolecular acylnitroso Diels-Alder approach". . p. 9213 - 9216. Retrieved 2007/10/02.