(3R,4R)-1-Boc-4-fluoro-3-piperidinol

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Cat Number

INT1314641025

CAS Number

1314641-02-5

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CAS Number

1314641-02-5

Synonyms

1-Piperidinecarboxylic acid, 4-fluoro-3-hydroxy-, 1,1-dimethylethyl ester, (3R,4R)-;(3R, 4R) -4-fluoro-3-hydroxypiperidine-1-carboxylic acid tert butyl ester

Molecular Formula

C10H18FNO3

Molecular Weight

219.25

Boiling Point

300.8℃

Relative Density

1.15

pKa

13.58

General Description

(3R,4R)-1-Boc-4-fluoro-3-piperidinol is a highly specialized chiral heterocyclic intermediate, specifically a piperidine derivative featuring a tert-butoxycarbonyl (Boc) protecting group at the nitrogen atom. Its molecular architecture is defined by a trans-configured fluorine atom at the C4 position and a hydroxyl group at C3, making it a critical building block for asymmetric synthesis.

Mechanism of Action

It functions as a rigid chiral scaffold in organic synthesis. The electronegative fluorine atom at the 4-position exerts a significant inductive effect, which modulates the hydrogen-bonding capability and the pKa of the adjacent secondary alcohol, while the Boc group ensures high regioselectivity during complex multi-step functionalization.

Application

It is primarily employed as a key intermediate in the pharmaceutical development of advanced kinase inhibitors and therapeutic candidates for neurological disorders where precise stereochemistry is vital for target binding.