(+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

Base Information

• Chemical Name: (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester
• CAS No.: 73053-73-3
• Molecular Formula: C₂₇H₃₅NO₅
• Molecular Weight: 453.579
• Mol file: 73053-73-3.mol

Synonyms:

Chemical Property of (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester

There total 29 articles about (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester 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: 74.0%

benzyl bromide (100-39-0) + (+/-)-trans-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester (73053-67-5,74282-33-0,74282-34-1) → (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester (73053-73-3,73650-71-2)

Guidance literature:

With potassium carbonate; In acetone; for 48h; Heating;

Reference yield:

2-(5-(benzyloxy)-4-methoxyphenyl)-ethan-1-ol (55323-55-2) → (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester (73053-73-3,73650-71-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 93 percent / N-bromosuccinimide, triphenylphosphine (Ph₃P) / benzene / 5 h / 10 - 20 °C

2: 10.8 g / benzene / 96 h / Heating

3: 8.27 g / K₃Fe(CN)6, KOH / H₂O; benzene / 5 h / 32 °C

4: 97 percent / H₂ / Raney Ni W-2 / ethanol / 13 h / Ambient temperature

5: 96 percent / aq. HCl (10percent) / ethanol / 2 h / 50 °C

6: 84 percent / aq. hydrazine hydrate (80percent), KOH / ethane-1,2-diol / 1.) 120 deg C, 1 h; 2.) 190 deg C, 3.5 h

7: 97 percent / K₂CO₃ / acetone / 30 h / Heating

8: 77 percent / lithium diisopropylamide (LDA), hexamethylphosphoramide (HMPA) / tetrahydrofuran / 2 h / -78 °C

9: 1.17 g / sodium metaperiodate (NaIO₄) / methanol; H₂O / 24 h / Ambient temperature

10: 631 mg / CaCO₃ / toluene / 1 h / Heating

11: 1.) Na-EtOH; 2.) aq. NaOH (1N) / 1.) EtOH, 70 deg C, 2 h, reflux, 6 h; 2.) EtOH, 50 deg C, 4 h

12: 59 percent / aq. AcOH (60percent) / 6 h / Heating

13: 91 percent / HCl / 24 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydroxide; sodium periodate; N-Bromosuccinimide; ethanol; hydrogen; sodium; potassium carbonate; hydrazine hydrate; acetic acid; triphenylphosphine; calcium carbonate; potassium hexacyanoferrate(III); lithium diisopropyl amide; Raney Ni W-2; In tetrahydrofuran; methanol; ethanol; water; ethylene glycol; acetone; toluene; benzene;

Reference yield:

4-[(3-benzyloxy-4-methoxy-phenyl)-thioacetyl]-morpholine (23428-78-6) → (+/-)-trans-1-(3-benzyloxy-4-methoxyphenethyl)-5-ethyl-2-oxo-4-piperidineacetic acid ethyl ester (73053-73-3,73650-71-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 25.0 g / aq. KOH (50percent) / ethanol / 9 h / Heating

2: 94 percent / HCl / 17 h / 30 °C

3: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

4: 93 percent / N-bromosuccinimide, triphenylphosphine (Ph₃P) / benzene / 5 h / 10 - 20 °C

5: 10.8 g / benzene / 96 h / Heating

6: 8.27 g / K₃Fe(CN)6, KOH / H₂O; benzene / 5 h / 32 °C

7: 97 percent / H₂ / Raney Ni W-2 / ethanol / 13 h / Ambient temperature

8: 96 percent / aq. HCl (10percent) / ethanol / 2 h / 50 °C

9: 84 percent / aq. hydrazine hydrate (80percent), KOH / ethane-1,2-diol / 1.) 120 deg C, 1 h; 2.) 190 deg C, 3.5 h

10: 97 percent / K₂CO₃ / acetone / 30 h / Heating

11: 77 percent / lithium diisopropylamide (LDA), hexamethylphosphoramide (HMPA) / tetrahydrofuran / 2 h / -78 °C

12: 1.17 g / sodium metaperiodate (NaIO₄) / methanol; H₂O / 24 h / Ambient temperature

13: 631 mg / CaCO₃ / toluene / 1 h / Heating

14: 1.) Na-EtOH; 2.) aq. NaOH (1N) / 1.) EtOH, 70 deg C, 2 h, reflux, 6 h; 2.) EtOH, 50 deg C, 4 h

15: 59 percent / aq. AcOH (60percent) / 6 h / Heating

16: 91 percent / HCl / 24 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium hydroxide; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; ethanol; hydrogen; sodium; potassium carbonate; hydrazine hydrate; acetic acid; triphenylphosphine; calcium carbonate; potassium hexacyanoferrate(III); lithium diisopropyl amide; Raney Ni W-2; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; ethylene glycol; acetone; toluene; benzene;

upstream raw materials:

benzyl bromide

(+/-)-trans-5-ethyl-1-(3-hydroxy-4-methoxyphenethyl)-2-oxo-4-piperidineacetic acid ethyl ester

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine

3-(α,α-ethyleenedithioethyl)pyridine

Downstream raw materials:

(+/-)-9-benzyloxy-N-(3-benzyloxy-4-methoxyphenethyl)-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetamide

(+/-)-9-benzyloxy-2β-(6-benzyloxy-3,4-dihydro-7-methoxy-1-isoquinolyl)methyl-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine

(+/-)-9-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetic acid

(+/-)-9-benzyloxy-3α-ethyl-1,3,4,6,7,11bα-hexahydro-10-methoxy-2H-benzoquinolizine-2β-acetic acid ethyl ester

Refernces

• 1、 Fujii, Tozo,Ohba, Masashi. "Quinolizidines. X. Stereospecific Synthesis of (+/-)-9-Demethylpsychotrine and (+/-)-10-Demethylpsychotrine". . p. 144 - 151. Retrieved 2007/10/02.