ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

Base Information

• Chemical Name: ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate
• CAS No.: 42191-83-3
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.321
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10441506
• Wikidata: Q82258294
• Mol file: 42191-83-3.mol

Synonyms:ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate;42191-83-3;ethyl spiro[1H-2-benzofuran-3,4'-piperidine]-1'-carboxylate;ethyl3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate;SCHEMBL11831680;DTXSID10441506;AMY36662;AKOS015843367;A6900;CS-0452346;FT-0682196;Ethyl-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate;Ethyl 1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate;ethyl 3H-spiro[isobenzo[b]furan-1,4'-piperidine]-1'-carboxylate;Spiro[isobenzofuran-1(3H),4'-piperidine]-1'-carboxylicacid,ethyl ester

Chemical Property of ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

Chemical Property:

• Boiling Point: 394.726 °C at 760 mmHg
• Flash Point: 192.524 °C
• PSA: 38.77000
• Density: 1.209 g/cm³
• LogP: 2.60230
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 261.13649347
• Heavy Atom Count: 19
• Complexity: 336

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1CCC2(CC1)C3=CC=CC=C3CO2

Technology Process of ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

There total 4 articles about ethyl 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-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: 100.0%

4-hydroxy-4-(2-hydroxymethyl-phenyl)-piperidine-1-carboxylic acid ethyl ester (71546-51-5) → 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylic acid ethyl ester (42191-83-3)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In toluene; at 60 ℃; for 0.5h;

Reference yield:

o-bromobenzyl alcohol (18982-54-2) → 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylic acid ethyl ester (42191-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) n-hexane, THF, Et₂O, -78 deg C, 1 h, 2.) n-hexane, THF, Et₂O, RT, 16 h

2: 81 percent / TsCl, pyridine / CH₂Cl₂ / 58 h / Ambient temperature

With pyridine; n-butyllithium; p-toluenesulfonyl chloride; In dichloromethane;

DOI:10.1248/cpb.46.351

Reference yield:

N-ethoxycarbonyl-4-piperidone (29976-53-2) → 3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylic acid ethyl ester (42191-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) n-hexane, THF, Et₂O, -78 deg C, 1 h, 2.) n-hexane, THF, Et₂O, RT, 16 h

2: 81 percent / TsCl, pyridine / CH₂Cl₂ / 58 h / Ambient temperature

With pyridine; n-butyllithium; p-toluenesulfonyl chloride; In dichloromethane;

DOI:10.1248/cpb.46.351

upstream raw materials:

4-hydroxy-4-(2-hydroxymethyl-phenyl)-piperidine-1-carboxylic acid ethyl ester

o-bromobenzyl alcohol

N-ethoxycarbonyl-4-piperidone

Refernces

• 1、 Kubota, Hirokazu,Fujii, Masahiro,Ikeda, Ken,Takeuchi, Makoto,Shibanuma, Tadao,Isomura, Yasuo. "Spiro-substituted piperidines as neurokinin receptor antagonists. I. Design and synthesis of (±)-N-[2-(3,4-Dichlorophenyl)-4- (spiro[isobenzofuran-1(3H),4'-piperidin]-1'-yl)butyl]-N-methylbenzamide, YM- 35375, as a new lead compound for novel neurokinin receptor antagonists". . p. 351 - 354. Retrieved 2007/10/03.