(2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one

Base Information

• Chemical Name: (2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one
• CAS No.: 122624-28-6
• Molecular Formula: C₂₄H₃₉NO₃
• Molecular Weight: 389.579
• Mol file: 122624-28-6.mol

Synonyms:(2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one

Chemical Property of (2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one

There total 10 articles about (2'R^*,6'S^*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-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'R*,6'S*)-(E)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>buten-2-one (122624-15-1) → (2'R*,6'S*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one (122624-28-6)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; for 0.583333h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo00279a034

Reference yield:

2-pentylcyclohexanone (32362-97-3) → (2'R*,6'S*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one (122624-28-6)

Guidance literature:

Multi-step reaction with 9 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

4: 2.) 2 N HCl / 1.) 150 deg C, 5 h, 2.) RT, overnight

5: 2.) triethylamine / 1.) dichloromethane, RT, overnight, 2.) RT, 1 h

6: 82 percent / Raney nickel W₂ / acetone / 2 h / Heating

7: 1.) bromine, 2.) triethylamine / 1.) ether, -70 deg C, 1.5 h, 2.) RT, 48 h

8: 68 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

9: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / 760 Torr / Ambient temperature

With Lawessons reagent; hydrogenchloride; potassium hydroxide; formic acid; potassium tert-butylate; hydrogen; bromine; triethylamine; hydroxylamine-O-sulfonic acid; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; ethyl acetate; acetone;

DOI:10.1021/jo00279a034

Reference yield:

7-pentylhexahydroazepin-2-one (84460-49-1) → (2'R*,6'S*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one (122624-28-6)

Guidance literature:

Multi-step reaction with 8 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

3: 2.) 2 N HCl / 1.) 150 deg C, 5 h, 2.) RT, overnight

4: 2.) triethylamine / 1.) dichloromethane, RT, overnight, 2.) RT, 1 h

5: 82 percent / Raney nickel W₂ / acetone / 2 h / Heating

6: 1.) bromine, 2.) triethylamine / 1.) ether, -70 deg C, 1.5 h, 2.) RT, 48 h

7: 68 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

8: H₂, KOH / 5percent Pd/C / ethyl acetate; ethanol / 0.58 h / 760 Torr / Ambient temperature

With Lawessons reagent; hydrogenchloride; potassium hydroxide; potassium tert-butylate; hydrogen; bromine; triethylamine; palladium on activated charcoal; Raney nickel W₂; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; ethyl acetate; acetone;

DOI:10.1021/jo00279a034

upstream raw materials:

(2'R^*,6'S^*)-(E)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>buten-2-one

2-pentylcyclohexanone

7-pentylhexahydroazepin-2-one

1-benzyl-7-pentylhexahydroazepin-2-one

Downstream raw materials:

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

(2R^*,6S^*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde