N-T-BOC-PYRROLE Chemical Properties

Boiling point:

91-92 °C20 mm Hg(lit.)

Density 

1 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4685(lit.)

Flash point:

167 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetonitrile, Dichloromethane, Ethyl Acetate, Methanol, Tetrahydrofuran

form 

Solution

pka

-6.10±0.70(Predicted)

color 

Colorless to yellow

InChI

InChI=1S/C9H13NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H,1-3H3

InChIKey

IZPYBIJFRFWRPR-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)C=CC=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

N-T-BOC-PYRROLE Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Pyrrole-1-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of pyrrole derived anti-cancer Agent.

Uses

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 drivatives
• N-boc-2-(4-methoxyphenyl)pyrrole
• N-boc-pyrrol-2-ylboronic acid

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 764, 1966 DOI: 10.1021/jo01341a027

General Description

N-Boc-pyrrole is an N-protected pyrrole. It undergoes Diels–Alder reaction with enantiomerically pure allene-1,3-dicarboxylates to form endo-adducts with retention in configurations at two newly generated stereogenic centers. It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane. Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported.

Synthesis

General procedure for the synthesis of tert-butyl 1-pyrrolecarboxylate from pyrrole and di-tert-butyl dicarbonate: di-tert-butyl dicarbonate (Boc2O, 9.8 g, 44.7 mmol) and triethylamine (TEA, 6.3 mL, 44.7 mmol) were added sequentially to a solution of pyrrole (3.0 g, 29.8 mmol) in dichloromethane (DCM, 15 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, extraction was performed with dichloromethane (2 x 400 mL) and water (400 mL). The organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to afford tert-butyl 1-pyrrolecarboxylate (26) as a white solid (7.5 g). Yield: 94%; 1H NMR (300 MHz, CDCl3) δ (ppm): 7.26 (s, 2H), 7.24 (t, J=2.4 Hz, 1H), 6.22 (t, J=2.4 Hz, 1H), 1.60 (d, J=11.7 Hz, 9H); ESI-MS [M+H]+=169.0.

References

[1] European Journal of Organic Chemistry, 2005, # 11, p. 2207 - 2212
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15739 - 15743
[3] Angew. Chem., 2015, vol. 127, # 52, p. 15965 - 15969,5
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1153 - 1164
[5] Medicinal Chemistry, 2018, vol. 14, # 5, p. 485 - 494

N-T-BOC-PYRROLE(5176-27-2)Related Product Information

• tert-butyl 3-endo-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
• 1-BOC-2,3-DIHYDRO-7-INDOLECARBALDEHYDE
• MORPHOLINE-3,4-DICARBOXYLIC ACID 4-TERT-BUTYL ESTER
• N-BOC-INDOLINE-7-CARBOXYLIC ACID
• 1-Boc-Pyrrolidine
• Fmoc-Trp(Boc)-OH
• TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE
• N-Boc-2-pyrroleboronic acid
• Z-TRP(BOC)-OH DCHA
• H-TRP(BOC)-OH
• Fmoc-D-Trp(Boc)-OH
• BOC-TRP(BOC)-OH
• 1-BOC-PYRROLE-2-BORONIC ACID, PINACOL ESTER
• H-D-TRP(BOC)-OH
• H-TRP(BOC)-OTBU HCL
• N-T-BOC-PYRROLE
• H-TRP(BOC)-2-CLTRT RESIN
• FMOC-TRP(BOC)-OPFP