N-T-BOC-PYRROLE

Base Information

• Chemical Name: N-T-BOC-PYRROLE
• CAS No.: 5176-27-2
• Molecular Formula: C9H13NO2
• Molecular Weight: 167.208
• Hs Code.: 2933990090
• Mol file: 5176-27-2.mol

Synonyms:Pyrrole-1-carboxylicacid, tert-butyl ester (7CI,8CI);1-(tert-Butoxycarbonyl)-1H-pyrrole;1-(tert-Butoxycarbonyl)pyrrole;1-Pyrrolecarboxylic acid tert-butyl ester;N-(tert-Butyloxycarbonyl)-1H-pyrrole;N-(tert-Butyloxycarbonyl)pyrrole;N-BOC-pyrrole;N-tert-Butoxycarbonyl-1H-pyrrole;N-tert-Butoxycarbonylpyrrole;tert-Butyl pyrrole-1-carboxylate;

Chemical Property of N-T-BOC-PYRROLE

Chemical Property:

• Vapor Pressure: 0.0977mmHg at 25°C
• Refractive Index: n20/D 1.4685(lit.)
• Boiling Point: 223.2 °C at 760 mmHg
• PKA: -6.10±0.70(Predicted)
• Flash Point: 88.8 °C
• PSA: 31.23000
• Density: 1 g/cm³
• LogP: 2.27130
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetonitrile, Dichloromethane, Ethyl Acetate, Methanol, Tetrahydrofuran

Purity/Quality:

99% ^*data from raw suppliers

Pyrrole-1-carboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Pyrrole-1-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of pyrrole derived anti-cancer Agent. N-Boc-pyrrole was used in the synthesis of 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid by treating with n-BuLi and subsequent reaction with trimethyl borate.It may be used as starting material in the synthesis of the following:tropane drivativesN-boc-2-(4-methoxyphenyl)pyrroleN-boc-pyrrol-2-ylboronic acid

Technology Process of N-T-BOC-PYRROLE

There total 6 articles about N-T-BOC-PYRROLE 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: 56.0%

dimethyl 7-(tert-butyloxycarbonyl)-7-azabicyclo<2.2.1.>-hepta-2,5-diene-2,3-dicarboxylate (114221-05-5) + phenylhydroxamoyl chloride (934-16-7) → 3-phenylisoxazole (1006-65-1) + N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + dimethyl 1-(tert-butyloxycarbonyl)-3,4-pyrroledicarboxylate (114221-06-6) + dimethyl 3-phenylisoxazole-4,5-dicarboxylate (7710-44-3)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo00245a026

Reference yield: 52.0%

N-(t-Butoxycarbonyl)-2,3-bis-7-azabicyclo<2.2.1>hepta-2,5-diene (82912-39-8) → 3-(2,4,6-trimethyl-phenyl)-isoxazole (49748-48-3) + N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + N-(t-Butoxycarbonyl)-2,3-bis-1H-pyrrole (82912-40-1) + 4,5-Bis-trifluoromethyl-3-(2,4,6-trimethyl-phenyl)-isoxazole

Guidance literature:

With mesitylenecarbonitrile oxide; In diethyl ether; at 30 ℃; for 24h;

DOI:10.1055/s-1982-29795

Reference yield:

para-iodoanisole (696-62-8) + N-(tert-butoxycarbonyl)-2-(trimethylstannyl)pyrrole (172282-33-6) → N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + 2-(4-methoxyphenyl)-1H-pyrrole-1-carboxylic acid 1,1-dimethylethyl ester (198981-85-0)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 24h; Heating;

DOI:10.1039/b505969k

upstream raw materials:

N-(t-Butoxycarbonyl)-2,3-bis-7-azabicyclo<2.2.1>hepta-2,5-diene

dimethyl 7-(tert-butyloxycarbonyl)-7-azabicyclo<2.2.1.>-hepta-2,5-diene-2,3-dicarboxylate

phenylhydroxamoyl chloride

(3-Methoxy-cyclohex-1-enesulfonyl)-benzene

Downstream raw materials:

3-bromo-7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester

endo-2-(p-tolyl-sulfone)-7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>hepta-2,5-diene

(1S,2R,3E,4R)-(-)-(l)-menthyl 7-tert-butoxycarbonyl-3-[2'-(l)-menthyloxy-2'-oxoethylidene]-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

(S_S)-2-(p-Tolylsulfinyl)pyrrole

Refernces

• 1、 Karaki, Fumika,Ohgane, Kenji,Imai, Hirotaka,Itoh, Kennosuke,Fujii, Hideaki. "Reactivity of 7-Azanorbornenes in Bioorthogonal Inverse Electron-Demand Diels–Alder Reactions". . p. 3815 - 3829. Retrieved 2017/07/22.
• 2、 Jin, Zhendong,Fuchs. "Addition of γ-methoxy allylsulfonyl anions to cyclopentenyl phenyl sulfones. A facile synthesis of β-cyclopentenyl-substituted dienones and trienones". . p. 3022 - 3028. Retrieved 2007/10/02.