tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate
• CAS No.: 209216-57-9
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• NSC Number: 716699
• DSSTox Substance ID: DTXSID201225708
• Mol file: 209216-57-9.mol

Synonyms:209216-57-9;tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate;1-Boc-1H-pyrrole-3-carbaldehyde;tert-butyl 3-formylpyrrole-1-carboxylate;3-Formyl-pyrrole-1-carboxylic acid tert-butyl ester;MFCD21337044;NSC716699;SCHEMBL14213918;DTXSID201225708;AC5467;NSC-716699;SB63882;BS-16564;SY235845;Pyrrole-3-aldehyde, N-t-butyloxycarbonyl-;CS-0154786;tert-Butyl3-formyl-1H-pyrrole-1-carboxylate;tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate #;3-Formylpyrrole-1-carboxylic acid tert-butyl ester;1,1-Dimethylethyl 3-formyl-1H-pyrrole-1-carboxylate

Chemical Property of tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate

Chemical Property:

• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

97% ^*data from raw suppliers

3-Formyl-pyrrole-1-carboxylicacidtert-butylester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC(=C1)C=O

Technology Process of tert-Butyl 3-formyl-1H-pyrrole-1-carboxylate

There total 1 articles about tert-Butyl 3-formyl-1H-pyrrole-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: 93.0%

pyrrole-3-carboxaldehyde (7126-39-8) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-formylpyrrole-1-carboxylate (209216-57-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; 0 deg C, 3 h then r.t., 1 h;

DOI:10.1016/S0040-4039(98)00722-9

Reference yield: 92.0%

phenylacetylene (536-74-3) + tert-butyl 3-formylpyrrole-1-carboxylate (209216-57-9) + methyl iodide (74-88-4) → tert-butyl 3-(1-methoxy-3-phenylprop-2-yn-1-yl)-1H-pyrrole-1-carboxylate

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

tert-butyl 3-formylpyrrole-1-carboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02628

Reference yield: 85.0%

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) + tert-butyl 3-formylpyrrole-1-carboxylate (209216-57-9) → 3-((E)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-pyrrole-1-carboxylic acid tert-butyl ester

Guidance literature:

With 1,1,3,3-tetramethylguanidine; In dichloromethane; -41 deg C, 1 h, r.t., 21 h then reflux, 12 h;

DOI:10.1016/S0040-4039(98)00722-9

upstream raw materials:

pyrrole-3-carboxaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

2-amino-3-(1H-pyrrol-3-yl)propanoic acid

3-(2-Benzyloxycarbonylamino-2-carboxy-ethyl)-pyrrole-1-carboxylic acid tert-butyl ester

3-(2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-pyrrole-1-carboxylic acid tert-butyl ester