rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine

Base Information

• Chemical Name: rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine
• CAS No.: 97827-15-1
• Molecular Formula: C₂₄H₃₉NO₅S
• Molecular Weight: 453.643
• Mol file: 97827-15-1.mol

Synonyms:

Chemical Property of rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine

There total 15 articles about rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine 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: 83.0%

rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-(3-hydroxyheptyl)-6-propylpiperidine (97827-12-8,122045-86-7) + methanesulfonyl chloride (124-63-0) → rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine (97827-15-1,122045-89-0)

Guidance literature:

With triethylamine; In dichloromethane; at -10 ℃; for 0.0833333h;

DOI:10.1021/jo00278a020

Reference yield:

ethyl (E)-2-heptenoate (54340-72-6) → rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine (97827-15-1,122045-89-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 80 percent / LiAlH₄, AlCl₃ / diethyl ether / 2 h / 0 °C

2: 65 percent / PBr₃ / petroleum ether / 2 h / -10 °C

3: 86 percent / benzene / 2 h / Heating

4: 1.) 1.6 M N-BuLi, 2.) HMPA / 1.) THF, hexane, -5 deg C, 20 min, 2.) -5 deg C, 1 h

5: 82 percent / KOH, 95percent EtOH / 1 h / Heating

6: oxalyl chloride / benzene / Ambient temperature

7: NH₂OH*HCl, Na₂CO₃ / CHCl₃; H₂O / 3 h / Heating

8: 82 percent / tetrapropylammonium periodate / CHCl₃ / 1 h / 0 °C

9: 90 percent / H₂ / 5percent Pd/C / methanol / 3 h

10: diethyl ether / 1 h / Ambient temperature

11: 10percent ethanolic HCl, NaBH₃CN / methanol / 0.5 h / 0 °C / pH 3.8 - 5.4

12: 85 percent / 60percent aq. AcOH, Zn / 9 h / 60 °C

13: 36 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

14: 83 percent / triethylamine / CH₂Cl₂ / 0.08 h / -10 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; ethanol; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; phosphorus tribromide; sodium cyanoborohydride; sodium carbonate; acetic acid; triethylamine; zinc; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform; water; Petroleum ether; benzene;

DOI:10.1021/jo00278a020

Reference yield:

(E)-1-bromo-2-heptene (35349-80-5) → rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-<3-<(methylsulfonyl)oxy>heptyl>-6-propylpiperidine (97827-15-1,122045-89-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 86 percent / benzene / 2 h / Heating

2: 1.) 1.6 M N-BuLi, 2.) HMPA / 1.) THF, hexane, -5 deg C, 20 min, 2.) -5 deg C, 1 h

3: 82 percent / KOH, 95percent EtOH / 1 h / Heating

4: oxalyl chloride / benzene / Ambient temperature

5: NH₂OH*HCl, Na₂CO₃ / CHCl₃; H₂O / 3 h / Heating

6: 82 percent / tetrapropylammonium periodate / CHCl₃ / 1 h / 0 °C

7: 90 percent / H₂ / 5percent Pd/C / methanol / 3 h

8: diethyl ether / 1 h / Ambient temperature

9: 10percent ethanolic HCl, NaBH₃CN / methanol / 0.5 h / 0 °C / pH 3.8 - 5.4

10: 85 percent / 60percent aq. AcOH, Zn / 9 h / 60 °C

11: 36 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

12: 83 percent / triethylamine / CH₂Cl₂ / 0.08 h / -10 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; n-butyllithium; oxalyl dichloride; ethanol; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; sodium cyanoborohydride; sodium carbonate; acetic acid; triethylamine; zinc; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform; water; benzene;

DOI:10.1021/jo00278a020

upstream raw materials:

rel-<2S,6S,2(3R)>-N-<(benzyloxy)carbonyl>-2-(3-hydroxyheptyl)-6-propylpiperidine

methanesulfonyl chloride

pentanal

ethyl (E)-2-heptenoate

Downstream raw materials:

gephyrotoxin 223AB