Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylate
• CAS No.: 203664-61-3
• Molecular Formula: C₁₂H₁₉Br₂NO₂
• Molecular Weight: 369.096
• DSSTox Substance ID: DTXSID90467087
• Mol file: 203664-61-3.mol

Synonyms:203664-61-3;TERT-BUTYL 4-(2,2-DIBROMOVINYL)PIPERIDINE-1-CARBOXYLATE;Tert-butyl 4-(2,2-dibromoethenyl)piperidine-1-carboxylate;1-Piperidinecarboxylic acid, 4-(2,2-dibromoethenyl)-, 1,1-dimethylethyl ester;SCHEMBL741520;DTXSID90467087;MBNHUCDXSFFRLG-UHFFFAOYSA-N;AMY35526;MFCD20528891;AKOS025291096;SB15821;1-Boc-4-(2,2-Dibromoethenyl)piperidine;AS-51498;CS-0036441;P12802;A814494;J-524585;1-(tert-butoxycarbonyl)-4-(2,2-dibromovinyl)piperidine;4-(2,2-dibromovinyl)-1-(tert-butoxycarbonyl)piperidine;1-(t-Butoxycarbonyl)-4-(2,2-dibromoethen-1-yl)piperidine;tert-butyl 4-(2, 2-dibromoethenyl)piperidine-1-carboxylate;1-(t-Butoxycarbonyl)-4-(2,2-dibromoethen-1-yl)-piperidine;TERT-BUTYL4-(2,2-DIBROMOVINYL)PIPERIDINE-1-CARBOXYLATE;4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylate

Chemical Property:

• PSA: 29.54000
• LogP: 4.20260
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 368.97620
• Heavy Atom Count: 17
• Complexity: 298

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl 4-(2,2-dibromoethenyl)piperidine-1-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(CC1)C=C(Br)Br

Technology Process of Tert-butyl 4-(2,2-dibromovinyl)piperidine-1-carboxylate

There total 5 articles about Tert-butyl 4-(2,2-dibromovinyl)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: 90.0%

carbon tetrabromide (558-13-4) + tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3) → 4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (203664-61-3)

Guidance literature:

carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.416667h;

tert butyl 4-formylpiperidine-1-carboxylate; In dichloromethane; at 0 ℃; for 0.833333h;

Reference yield:

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4,174286-31-8) → 4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (203664-61-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / BH₃*THF / tetrahydrofuran

2: 86 percent / oxalyl chloride; Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 - 20 °C

3: Ph₃P / CH₂Cl₂

With borane-THF; oxalyl dichloride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2003.12.006

Reference yield:

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate (123855-51-6) → 4-(2,2-dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester (203664-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / oxalyl chloride; Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 - 20 °C

2: Ph₃P / CH₂Cl₂

With oxalyl dichloride; triethylamine; triphenylphosphine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2003.12.006

upstream raw materials:

carbon tetrabromide

tert butyl 4-formylpiperidine-1-carboxylate

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate

Downstream raw materials:

tert-butyl 4-(3-hydroxyprop-1-yn-1-yl)piperidine-1-carboxylate

tert-butyl 4-(3-hydroxyisoxazol-5-yl)piperidine-1-carboxylate

4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester

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