1121057-75-7 | 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, HCl

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$12.00	$9.00
5g	98%	in stock	$59.00	$42.00
10g	98%	in stock	$88.00	$62.00
25g	98%	in stock	$207.00	$145.00

Description

• Catalog Number: AB51533
• Chemical Name: 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, HCl
• CAS Number: 1121057-75-7
• Molecular Formula: C11H21BClNO2
• Molecular Weight: 245.5539
• MDL Number: MFCD11506076
• SMILES: CC1(C)OB(OC1(C)C)C1=CCNCC1.Cl

Computed Properties

• Complexity: 270
• Covalently-Bonded Unit Count: 2
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1

Upstream Synthesis Route

The synthesis of 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, starting from commercially available materials, proceeds as follows:

1. Begin with the preparation of 1,2,3,6-tetrahydropyridine via a hydrogenation reaction of pyridine using a suitable catalyst such as Palladium on carbon (Pd/C) under hydrogen atmosphere.

2. Functionalize the 4-position by performing a halogenation, typically bromination, using N-bromosuccinimide (NBS) in the presence of a radical initiator such as AIBN (azobisisobutyronitrile) to yield 4-bromo-1,2,3,6-tetrahydropyridine.

3. Conduct a boronic ester synthesis by treating the 4-bromo-1,2,3,6-tetrahydropyridine with an organoborane source, such as bis(pinacolato)diboron, in the presence of a palladium catalyst (e.g., Pd(dppf)Cl2) and a base (e.g., potassium acetate) under suitable conditions to introduce the boronic ester functionality, yielding 1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester.

4. Finally, to obtain the hydrochloride salt form, treat the boronic ester with hydrogen chloride in an appropriate solvent like diethyl ether or dichloromethane to afford 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, HCl.

Each step should be followed by appropriate purification techniques, such as column chromatography, to isolate the desired product before moving on to the next step. It is important to control reaction conditions such as temperature and solvent choice to ensure selectivity and maximize yields.