Benzyl 4-iodopiperidine-1-carboxylate

Base Information

• Chemical Name: Benzyl 4-iodopiperidine-1-carboxylate
• CAS No.: 885275-00-3
• Molecular Formula: C13H16 I N O2
• Molecular Weight: 345.18
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID90693066
• Nikkaji Number: J3.295.463D
• Wikidata: Q82622089
• Mol file: 885275-00-3.mol

Synonyms:885275-00-3;BENZYL 4-IODOPIPERIDINE-1-CARBOXYLATE;N-CBZ-4-IODOPIPERIDINE;1-Cbz-4-iodopiperidine;SCHEMBL2630944;DTXSID90693066;MSRXUEGQXJQJJX-UHFFFAOYSA-N;MFCD04115043;AKOS015836794;1-(Benzyloxycarbonyl)-4-iodopiperidine;CS-W006399;DS-7854;PB24852;BENZYL4-IODOPIPERIDINE-1-CARBOXYLATE;FT-0720939;P10293;EN300-7382401;A862006

Chemical Property of Benzyl 4-iodopiperidine-1-carboxylate

Chemical Property:

• PSA: 29.54000
• LogP: 3.16050
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 345.02258
• Heavy Atom Count: 17
• Complexity: 246

Purity/Quality:

98% ^*data from raw suppliers

N-CBZ-4-Iodopiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCC1I)C(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 4-iodopiperidine-1-carboxylate

There total 2 articles about Benzyl 4-iodopiperidine-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: 84.0%

1-(benzyloxycarbonyl)-4-hydroxypiperidine (95798-23-5) → 4-iodo-piperidine-1-carboxylic acid benzyl ester (885275-00-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 18.33h;

DOI:10.1021/jm500713j

Reference yield: 70.0%

1-benzyl 4-(1,3-dioxoisoindolin-2-yl) piperidine-1,4-dicarboxylate → 4-iodo-piperidine-1-carboxylic acid benzyl ester (885275-00-3)

Guidance literature:

With triphenylphosphine; lithium iodide; In acetone; at 28 ℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1021/acs.orglett.0c03173

Reference yield: 95.0%

4-iodo-piperidine-1-carboxylic acid benzyl ester (885275-00-3) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (R)-benzyl 4-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)piperidine-1-carboxylate (1448219-24-6)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In diethyl ether; cyclohexane; at -78 ℃; for 3.5h; Inert atmosphere;

With zinc(II) iodide; In tetrahydrofuran; diethyl ether; cyclohexane; at -78 - 20 ℃; for 1.5h; Cooling with acetone-dry ice; Inert atmosphere;

4-iodo-piperidine-1-carboxylic acid benzyl ester; With (1,2-dimethoxyethane)dichloronickel(II); (1R,2R)-N,N’-dimethyl-1,2-di(naphthalen-1-yl)ethane-1,2-diamine; In tetrahydrofuran; diethyl ether; cyclohexane; at 20 ℃; for 60h; Reagent/catalyst; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja4054114

upstream raw materials:

1-(benzyloxycarbonyl)-4-hydroxypiperidine

Downstream raw materials:

C₂₆H₄₁NO₂Si

benzyl 4-(3-phenylpropyl)piperidine-1-carboxylate

4-benzoylpiperidine-1-carboxylic acid benzyl ester

(R)-benzyl 4-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)piperidine-1-carboxylate