188975-88-4 | N-Boc-hexahydro-1H-azepin-4-one

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$6.00	$4.00
1g	95%	in stock	$7.00	$5.00
5g	95%	in stock	$14.00	$10.00
10g	95%	in stock	$24.00	$17.00
25g	95%	in stock	$52.00	$36.00
100g	95%	in stock	$157.00	$110.00
250g	95%	in stock	$343.00	$240.00

Description

• Catalog Number: AB77135
• Chemical Name: N-Boc-hexahydro-1H-azepin-4-one
• CAS Number: 188975-88-4
• Molecular Formula: C11H19NO3
• Molecular Weight: 213.2735
• MDL Number: MFCD03788435
• SMILES: O=C1CCCN(CC1)C(=O)OC(C)(C)C

Computed Properties

• Complexity: 255
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• XLogP3: 0.9

Upstream Synthesis Route

The upstream synthesis route of N-Boc-hexahydro-1H-azepin-4-one involves several key steps, starting from readily available starting materials.

1. **Preparation of the Azepine Ring**: Begin with the cyclization of a di-functionalized amino ester, such as 2-(2-aminoethyl)malonic acid diethyl ester, to form the seven-membered azepine ring. This can be achieved through an intramolecular cyclization reaction facilitated by the use of acid catalysts or via thermal conditions.

2. **Reduction to Hexahydroazepinone**: The cyclic azepine is then subjected to hydrogenation to fully reduce any unsaturation, translating to a saturated hexahydro-1H-azepin-4-one core. This is typically done using a catalyst such as Pd/C under hydrogen pressure.

3. **Boc Protection**: The final step involves the protection of the amine functionality. The free amine of hexahydro-1H-azepin-4-one is treated with di-tert-butyl dicarbonate (Boc2O) in the presence of a base like triethylamine (Et3N) to generate the target molecule, N-Boc-hexahydro-1H-azepin-4-one. The reaction proceeds through the formation of an O-acylisourea intermediate, which then reacts with the free amine to give the desired Boc-protected amine.

Purification is typically conducted via crystallization or chromatography, depending on the specific impurities and byproducts present. Each step must be carefully controlled and optimized for yield, purity, and stereoselectivity where relevant.