tert-Butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate
• CAS No.: 50585-36-9
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.261
• DSSTox Substance ID: DTXSID70575174
• Nikkaji Number: J763.062J
• Wikidata: Q82464454
• Mol file: 50585-36-9.mol

Synonyms:50585-36-9;tert-Butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate;TERT-BUTYL 2,5-DIMETHYLPYRROLE-1-CARBOXYLATE;SCHEMBL3188741;2,5-dimethyl-pyrrole-1-carboxylic acid tert-butyl ester;DTXSID70575174;GWXRCRIYSPTHPL-UHFFFAOYSA-N

Chemical Property of tert-Butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 195.125928785
• Heavy Atom Count: 14
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(N1C(=O)OC(C)(C)C)C

Technology Process of tert-Butyl 2,5-dimethyl-1H-pyrrole-1-carboxylate

There total 1 articles about tert-Butyl 2,5-dimethyl-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:

C20H25NO4S + N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester (172749-96-1) → 1-<(1,1-dimethylethoxy)carbonyl>-2,5-dimethylpyrrole (50585-36-9) + C18H25NO6S2

Guidance literature:

In chloroform-d1; at 37 ℃;

DOI:10.1039/c9sc00125e

Reference yield: 82.0%

1-<(1,1-dimethylethoxy)carbonyl>-2,5-dimethylpyrrole (50585-36-9) → 2,5-dimethyl-1-hydroxymethylpyrrole (143756-01-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 50 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2009.10.025

Reference yield:

1-<(1,1-dimethylethoxy)carbonyl>-2,5-dimethylpyrrole (50585-36-9) → cis-N-benzyl-2,5-dimethylpyrrolidine (4209-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / H₂ / 5percent Pt/C / methanol / 1.5 h / 760 Torr / Ambient temperature

2: 2N methanolic hydrochloric acid / 2.5 h / Heating

3: sodium carbonate / acetone / 2 h / Heating

With hydrogenchloride; hydrogen; sodium carbonate; platinum on activated charcoal; In methanol; acetone;

DOI:10.1021/jo00196a020

upstream raw materials:

N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester

Downstream raw materials:

cis-N-benzyl-2,5-dimethylpyrrolidine

(2R,5S)-2,5-dimethyltetrahydro-1H-1-pyrrolylidium chloride

2,5-dimethyl-1-hydroxymethylpyrrole