(R)-Ethyl 3-benzylpiperidine-3-carboxylate

Base Information

• Chemical Name: (R)-Ethyl 3-benzylpiperidine-3-carboxylate
• CAS No.: 170844-43-6
• Molecular Formula: C15H21NO2
• Molecular Weight: 247.33300
• DSSTox Substance ID: DTXSID10441127
• Wikidata: Q82257738
• Mol file: 170844-43-6.mol

Synonyms:(R)-Ethyl 3-benzylpiperidine-3-carboxylate;170844-43-6;ETHYL (3R)-3-BENZYLPIPERIDINE-3-CARBOXYLATE;(R)-Ethyl3-benzylpiperidine-3-carboxylate;DTXSID10441127;CS-M2150;AKOS015969436;SB48601;CS-14610;ethyl (R)-3-benzylpiperidine-3-carboxylate;C12575

Chemical Property of (R)-Ethyl 3-benzylpiperidine-3-carboxylate

Chemical Property:

• Boiling Point: 343.7±35.0 °C(Predicted)
• PKA: 9.35±0.10(Predicted)
• PSA: 38.33000
• Density: 1.059±0.06 g/cm3(Predicted)
• LogP: 2.49080
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 247.157228913
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

98%min ^*data from raw suppliers

(R)-Ethyl3-benzylpiperidine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(CCCNC1)CC2=CC=CC=C2
• Isomeric SMILES: CCOC(=O)[C@]1(CCCNC1)CC2=CC=CC=C2

Technology Process of (R)-Ethyl 3-benzylpiperidine-3-carboxylate

There total 17 articles about (R)-Ethyl 3-benzylpiperidine-3-carboxylate 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: 85.0%

→ (S)-3-carbethoxy-3-benzylpiperidine (170844-45-8,170844-43-6)

Guidance literature:

Reference yield:

diethyl 2-benzyl-2-(2-cyanoethyl)malonate (10444-15-2) → (S)-3-carbethoxy-3-benzylpiperidine (170844-45-8,170844-43-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

2: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

3: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

4: TFA / CH₂Cl₂ / 1.5 h / 40 °C

5: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

6: Lawesson's reagent / toluene / 2 h / 110 °C

7: 100 mg / NaBH₄, Raney Ni / tetrahydrofuran; ethanol; H₂O / 0.25 h

With Lawessons reagent; hydrogenchloride; porcine liver esterase; dmap; sodium tetrahydroborate; phosphate buffer; hydrogen; nickel; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo980990v

Reference yield:

diethyl 2-benzylmalonate (607-81-8) → (S)-3-carbethoxy-3-benzylpiperidine (170844-45-8,170844-43-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / EtONa, MTBE / ethanol / 1 h / 40 °C

2: 70 percent / H₂, aq. HCl / Pd(OH)2 / ethanol / 22 h / 50 °C / 2172.02 Torr

3: 89 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

4: phosphate buffer, porcine liver esterase / H₂O / 27 h / 37 °C

5: TFA / CH₂Cl₂ / 1.5 h / 40 °C

6: DCC, DIEA, HOBT, DMAP / CH₂Cl₂ / 20 h / 25 °C

7: Lawesson's reagent / toluene / 2 h / 110 °C

8: 100 mg / NaBH₄, Raney Ni / tetrahydrofuran; ethanol; H₂O / 0.25 h

With Lawessons reagent; hydrogenchloride; porcine liver esterase; dmap; sodium tetrahydroborate; phosphate buffer; tert-butyl methyl ether; hydrogen; sodium ethanolate; nickel; benzotriazol-1-ol; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo980990v

upstream raw materials:

3-Benzylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

ethyl N-(t-butyloxycarbonyl)nipecotate

Ethyl nipecotate

3-Benzyl-piperidine-3-carboxylic acid ethyl ester

Downstream raw materials:

(S)-3-carbethoxy-3-benzylpiperidine

Refernces

• 1、 Yang, Lihu,Morriello, Greg,Patchett, Arthur A.,Leung, Kwan,Jacks, Tom,Cheng, Kang,Schleim, Klaus D.,Feeney, William,Chan, Wanda W.-S.,Chiu, Shuet-Hing L.,Smith, Roy G.. "1-[2(R)-(2-amino-2-methylpropionyl-amino)-3-(1H-indol-3-yl)propionyl]- 3-benzylpiperidine-3(S)-carboxylic acid ethyl ester (L-163,540): A potent, orally bioavailable, and short-duration growth hormone secretagogue [1]". . p. 2439 - 2441. Retrieved 2007/10/03.
• 2、 -. "Piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone". . . Retrieved 2008/06/13.