(2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one

Base Information

• Chemical Name: (2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one
• CAS No.: 122624-25-3
• Molecular Formula: C₂₆H₃₉NO
• Molecular Weight: 381.602

Synonyms:(2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one

Chemical Property of (2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one

There total 16 articles about (2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one 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:

2-pentylcyclohexanone (32362-97-3) → (2R*,6R*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one (122624-25-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 71 percent / hydroxylamine-O-sulfonic acid, formic acid / 1 h / Heating

2: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h

3: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

5: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

6: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

7: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

8: 59 percent / toluene / 40 h / 110 °C

9: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

10: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

11: Dibal / diethyl ether; toluene / 6 h / -78 °C

12: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

13: 4 M HCl / 3 h

14: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

15: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

16: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

With Lawessons reagent; hydrogenchloride; potassium hydroxide; copper(l) iodide; formic acid; Phenylselenyl chloride; oxalyl dichloride; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; hydroxylamine-O-sulfonic acid; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1021/jo00279a034

Reference yield:

7-pentylhexahydroazepin-2-one (84460-49-1) → (2R*,6R*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one (122624-25-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) t-BuOK / 1.) THF, RT, 10 min, 2.) THF, reflux, 1 h

2: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

4: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

5: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

6: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

7: 59 percent / toluene / 40 h / 110 °C

8: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

9: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

10: Dibal / diethyl ether; toluene / 6 h / -78 °C

11: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

12: 4 M HCl / 3 h

13: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

14: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

15: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

With Lawessons reagent; hydrogenchloride; potassium hydroxide; copper(l) iodide; Phenylselenyl chloride; oxalyl dichloride; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1021/jo00279a034

Reference yield:

1-benzyl-7-pentylhexahydroazepin-2-one (122624-02-6) → (2R*,6R*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-en-9-one (122624-25-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 95 percent / Lawesson's reagent / hexamethylphosphoric acid triamide / 2.5 h / 100 °C

3: 2.) triethylamine / 1.) 65-70 deg C, 3 h, 2.) dichloromethane, RT, 1 h

4: 98 percent / Raney nickel W₂ / acetone / 4 h / Heating

5: 1.) bromine, 2.) water, triethylamine / 1.) ether, dichloromethane, -70 deg C, 1.5 h, 2.) RT, 2 h

6: 59 percent / toluene / 40 h / 110 °C

7: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / Ambient temperature

8: 82 percent / p-toluenesulfonic acid / toluene / 6 h / Heating

9: Dibal / diethyl ether; toluene / 6 h / -78 °C

10: oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -60 °C

11: 4 M HCl / 3 h

12: 73 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

13: 1.) copper(I) iodide, 2.) triethylamine / 1.) ether, hexane, -30 deg C, 15 min, 2.) from -78 deg C to RT, 1.5 h

14: 1.) benzeneselenenyl chloride, 2.) H₂O₂, glacial acetic acid / 1.) THF, a) -78 deg C, 5 min, b) RT, 15 min, 2.) THF, H₂O, RT, 15 min

With Lawessons reagent; hydrogenchloride; potassium hydroxide; copper(l) iodide; Phenylselenyl chloride; oxalyl dichloride; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1021/jo00279a034

upstream raw materials:

(2R,6R)-1-Benzyl-7-butyl-2-pentyl-9-trimethylsilanyloxy-1-aza-spiro[5.5]undec-8-ene

2-pentylcyclohexanone

7-pentylhexahydroazepin-2-one

1-benzyl-7-pentylhexahydroazepin-2-one

Downstream raw materials:

(2R^*,6R^*)-1-benzyl-7-butyl-2-pentyl-1-azaspiro<5.5>undec-7-ene

perhydrohistrionicotoxin

2,6-epiperhydrohistrionicotoxin

1-benzyl-2,6-epiperhydrohistrionicotoxin

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