252720-32-4 | 4-tert-Butoxycarbonylamino-piperidine-1,4-dicarboxylic acid monobenzyl ester

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$53.00	$37.00
250mg	95%	in stock	$99.00	$69.00
500mg	95%	in stock	$187.00	$131.00
1g	95%	in stock	$194.00	$136.00
5g	95%	in stock	$675.00	$473.00
25g	95%	in stock	$2,317.00	$1,622.00

Description

• Catalog Number: AD57305
• Chemical Name: 4-tert-Butoxycarbonylamino-piperidine-1,4-dicarboxylic acid monobenzyl ester
• CAS Number: 252720-32-4
• Molecular Formula: C19H26N2O6
• Molecular Weight: 378.4195
• MDL Number: MFCD03425219
• SMILES: O=C(N1CCC(CC1)(NC(=O)OC(C)(C)C)C(=O)O)OCc1ccccc1

Upstream Synthesis Route

To synthesize 4-tert-Butoxycarbonylamino-piperidine-1,4-dicarboxylic acid monobenzyl ester, one must identify a suitable starting material and subsequent synthetic steps to introduce the appropriate functional groups while preserving the piperidine ring structure.

Starting with piperidine-1,4-dicarboxylic acid as the base structure, the synthetic route would proceed as follows:

1. Protection of one carboxylic acid group: To prevent reactions on both carboxylic acid groups during the synthesis, selectively protect one of the groups using a benzyl ester protecting group. This can be achieved by reacting piperidine-1,4-dicarboxylic acid with benzyl alcohol in the presence of a condensation agent such as DCC (dicyclohexylcarbodiimide) and a catalytic amount of DMAP (4-dimethylaminopyridine). The reaction should be carried out under anhydrous conditions, and the mono-protected product should be purified by column chromatography.

2. Introduction of Boc-protected amine: With the benzyl ester protected, react the free carboxyl group of the piperidine with a tert-butyl carbamate (Boc) protected amine, like tert-butyl carbamate itself. Utilize a coupling reagent such as EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) in the presence of HOBt (1-Hydroxybenzotriazole) to form the amide bond, generating 1-benzyl piperidine-4-carboxylic acid with the Boc-protected amino group.

3. Final deprotection: To obtain the target compound, the Boc protecting group must be removed from the amine without affecting the benzyl ester. This can be accomplished by treating the compound with a strong acid like hydrochloric acid in the presence of an inert solvent, which cleaves the Boc group, yielding the desired final product, 4-tert-Butoxycarbonylamino-piperidine-1,4-dicarboxylic acid monobenzyl ester.

Each step requires careful consideration of reaction conditions, reagent choice, and purification techniques to ensure a high-yield and purity of the desired product. The final product should be characterized using NMR, IR, and LC-MS to confirm the structure and purity.