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

Base Information

• Chemical Name: (2R^*,6S^*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde
• CAS No.: 122624-24-2
• Molecular Formula: C₂₂H₃₃NO₂
• Molecular Weight: 343.51
• Mol file: 122624-24-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about (2R^*,6S^*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde 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: 87.0%

(2'R*,6'S*)-4-<1'-benzyl-2'-(dimethoxymethyl)-6'-pentylpiperidin-2'-yl>butan-2-one (122624-28-6) → (2R*,6S*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde (122624-24-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; benzene; at 50 ℃; for 12h;

DOI:10.1021/jo00279a034

Reference yield:

2-pentylcyclohexanone (32362-97-3) → (2R*,6S*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde (122624-24-2)

Guidance literature:

Multi-step reaction with 10 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

10: 87 percent / p-toluenesulfonic acid / benzene; acetone / 12 h / 50 °C

With Lawessons reagent; hydrogenchloride; potassium hydroxide; formic acid; potassium tert-butylate; hydrogen; bromine; toluene-4-sulfonic acid; 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; benzene;

DOI:10.1021/jo00279a034

Reference yield:

2-pentylcyclohexanone (32362-97-3) → (2R*,6R*)-1-benzyl-2-(3-oxobutyl)-6-pentylpiperidine-2-carbaldehyde (122624-24-2)

Guidance literature:

Multi-step reaction with 13 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

With Lawessons reagent; hydrogenchloride; potassium hydroxide; formic acid; oxalyl dichloride; potassium tert-butylate; water; hydrogen; bromine; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; hydroxylamine-O-sulfonic acid; palladium on activated charcoal; Raney nickel W₂; In 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-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-6-pentyl-piperidine-2-carbaldehyde

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

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

(2R,6R)-1-Benzyl-7-butyl-2-pentyl-1-aza-spiro[5.5]undec-7-en-9-ol

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