(R)-tert-Butyl (azetidin-2-ylmethyl)carbamate Hydrochloride

Tert-Butyl N-[[(2R)-azetidin-2-yl]methyl]carbamate hydrochloride is a white to off-white crystalline powder.It should be stored at 2-8°C.The melting point is between 178 and 182°C.The compound exhibits slight solubility in water and is readily soluble in polar organic solvents like methanol,ethanol,THF,and DMF.It shows moderate solubility in ethyl acetate and dichloromethane and is insoluble in n-hexane.As a hydrochloride salt of a Boc-protected aminoazetidine,it is stable under dry,inert conditions.The Boc group is acid-labile,and the salt form makes it hygroscopic;it should be protected from moisture.

Tert-Butyl N-[[(2R)-azetidin-2-yl]methyl]carbamate hydrochloride(CAS No.1818843-14-9)is a chiral,protectedβ-amino acid derivative where the amino group is part of an azetidine(4-membered nitrogen heterocycle)ring.The structure features a primary amine(protected as Boc-carbamate)on a methylene linker attached to the azetidine ring.This constrained,chiral diamine is valuable for introducing conformational restraint.

1.Building Block forβ-Lactamase Inhibitor Analogs
The azetidine ring is a core isostere of theβ-lactam ring.This compound is used to synthesize non-β-lactam inhibitors of serineβ-lactamases(e.g.,KPC-2,CTX-M-15)by elaborating the methylene amine into boronic acid or sulfonate groups that mimic the transition state ofβ-lactam hydrolysis.

2.Chiral Solvent Additive for NMR Chiral Discrimination
The free diamine(after salt break and Boc deprotection)is used as a chiral solvating agent(CSA)for NMR spectroscopy.It effectively complexes with carboxylic acids and phosphinates,causing significant chemical shift non-equivalence(Δδ)of enantiomer protons,enabling rapid ee determination without derivatization.

3.Cross-linker for pH-Sensitive Hydrogels
The two amine groups(after deprotection)are reacted with PEG-based bis-N-hydroxysuccinimide(NHS)esters to form hydrogels.The azetidine ring introduces strain,and the gel's degradation rate is pH-dependent due to the protonation state of the remaining secondary amine,useful for controlled drug release in acidic tumor microenvironments.

4.Ligand for CO₂Capture and Conversion
The diamine is functionalized onto mesoporous silica.The primary amine reacts with CO₂to form a carbamate,while the strained azetidine secondary amine may activate CO₂for subsequent reactions.This material is studied for post-combustion carbon capture and as a heterogeneous catalyst for synthesizing cyclic carbonates from epoxides and CO₂.