392331-66-7 | tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$20.00	$14.00
5g	97%	in stock	$61.00	$43.00

Description

• Catalog Number: AD34076
• Chemical Name: tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate
• CAS Number: 392331-66-7
• Molecular Formula: C11H22N2O3
• Molecular Weight: 230.304
• MDL Number: MFCD11579803
• SMILES: NCC1(O)CCN(CC1)C(=O)OC(C)(C)C

Computed Properties

• Complexity: 252
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 3
• XLogP3: -0.1

Upstream Synthesis Route

The upstream synthesis route of tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate involves several key steps starting with the appropriate cyclization reaction to construct the piperidine ring, followed by functional group transformations to introduce the hydroxy, carboxylate, and aminomethyl groups onto the ring. Here is a concise route:

1. **Cyclization to form Piperidine Ring**: Start with a diene system such as 1,5-diketone, and through an aminocatalyzed Michael addition followed by a cyclization step, form the piperidine ring.

2. **Reduction of Ketone**: On the 1,5-diketone-derived piperidine, reduce one of the ketone groups to an alcohol using a reducing agent such as sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4).

3. **Protection of Hydroxy Group**: Protect the hydroxy group on the piperidine ring using a tert-butyloxycarbonyl (Boc) group to withstand further synthetic steps. This can be achieved using di-tert-butyl dicarbonate (Boc2O) in the presence of a base like triethylamine (Et3N).

4. **Aminomethylation**: Introduce the aminomethyl group on the piperidine ring through reductive amination, using formaldehyde and a selective reducing agent, where the primary amine can be generated in situ and then undergoes reductive alkylation.

5. **Esterification**: Convert the remaining ketone on the piperidine ring to its corresponding ester group using an esterification reaction with tert-butanol in the presence of an acid catalyst or an appropriate coupling reagent if direct esterification is challenging.

6. **Deprotection (if necessary)**: In case the protection of the hydroxy group is not compatible with the esterification conditions, deprotect it accordingly after esterification is complete.

Each step should be followed by appropriate work-up and purification procedures, such as extraction, column chromatography, or crystallization, to obtain the desired intermediate before proceeding to the next reaction. The order of the steps may vary depending on the specific conditions and reactivity of the intermediates involved.