135884-31-0 | 1-BOC-pyrrole-2-boronic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$8.00	$5.00
5g	98%	in stock	$18.00	$12.00
10g	98%	in stock	$30.00	$21.00
25g	98%	in stock	$47.00	$33.00

Description

• Catalog Number: AB51370
• Chemical Name: 1-BOC-pyrrole-2-boronic acid
• CAS Number: 135884-31-0
• Molecular Formula: C9H14BNO4
• Molecular Weight: 211.0228
• MDL Number: MFCD01318939
• SMILES: OB(c1cccn1C(=O)OC(C)(C)C)O

Computed Properties

• Complexity: 239
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 3

Upstream Synthesis Route

The synthesis of 1-BOC-pyrrole-2-boronic acid typically begins with the derivatization of pyrrole to protect the NH group, followed by the introduction of the boronic acid functionality:

1. Protection of NH:
Pyrrole is reacted with di-tert-butyl dicarbonate (BOC anhydride) in the presence of a base such as sodium hydride (NaH) or triethylamine (Et3N) to yield N-BOC-pyrrole. This step ensures that the NH group does not interfere with subsequent reactions.

2. Halogenation:
The 2-position of the N-BOC-pyrrole is then halogenated, usually by bromination using N-bromosuccinimide (NBS) in the presence of a radical initiator like azobisisobutyronitrile (AIBN) under light or heat to afford N-BOC-2-bromopyrrole.

3. Boronation:
The final step involves the conversion of the bromo group to a boronic acid group through a boronation reaction. This can be achieved by treating the N-BOC-2-bromopyrrole with a boronic acid, such as bis(pinacolato)diboron, in the presence of a palladium catalyst (e.g., Pd(PPh3)4) and a suitable base like potassium acetate (KOAc) in a solvent such as 1,4-dioxane or toluene. The reaction typically proceeds through a Suzuki-Miyaura cross-coupling mechanism to give the desired 1-BOC-pyrrole-2-boronic acid.

The obtained product is typically purified by chromatography or crystallization, depending on the specific conditions and byproducts formed during the synthesis. Each step in the reaction should be monitored by appropriate analytical techniques like NMR and GC-MS to ensure the purity and proper identification of intermediates and the final product.

Literature

• tert-Butyl 2-borono-1H-pyrrole-1-carboxyl-ate.

  Acta crystallographica. Section E, Structure reports online 20090401

• tert-Butyl 2-(dihydroxyboryl)pyrrole-1-carboxylate.

  Acta crystallographica. Section E, Structure reports online 20080601

• Application of a 6pi-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues.

  The Journal of organic chemistry 20070622

• Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai.

  Organic letters 20060330