325775-44-8

Basic information

• Product Name: 1-Boc-3-(Aminomethyl)azetidine
• Synonyms: TERT-BUTYL 3-(AMINOMETHYL)AZETIDINE-1-CARBOXYLATE;1-N-BOC-3-AMINOMETHYL AZETIDINE;1-BOC-3-(AMINOMETHYL)AZETIDINE;3-AMINOMETHYL-1-N-BOC-AZETIDINE;3-AMINOMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-BOC-3-AMINOMETHYLAZETIDINE,98+%;1-Boc-aminoazetidine;1-Boc-3-Aminomethylazetidine HCl
• CAS NO: 325775-44-8
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25
• Product Categories: pharmacetical;Aminomethyl's;Azetidine;Ring Systems
• Mol File: 325775-44-8.mol

Chemical Properties

• Boiling Point: 260.583 °C at 760 mmHg
• Flash Point: >110 °C
• Appearance: /
• Density: 1.0234 g/mL at 25 °C
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.4670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.97±0.29(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-Boc-3-(Aminomethyl)azetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-3-(Aminomethyl)azetidine(325775-44-8)
• EPA Substance Registry System: 1-Boc-3-(Aminomethyl)azetidine(325775-44-8)

Safety Data

• Hazard Codes: C,T
• Statements: 36/37/38-25
• Safety Statements: 26-36/37/39-45
• RIDADR: 2810
• WGK Germany: 1
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 325775-44-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Boc-3-(Aminomethyl)azetidine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures. The presence of the Boc group allows for selective reactions to occur without affecting the amine functionality, which is crucial for the development of new drugs with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 1-Boc-3-(Aminomethyl)azetidine is utilized as a building block for creating a wide range of organic molecules. The Boc protecting group facilitates controlled reactions, ensuring that the amine group remains intact and unreacted until it is specifically deprotected, allowing for precise control over the synthetic process.
Used in Research and Development:
1-Boc-3-(Aminomethyl)azetidine is employed in research and development settings as a model compound for studying the reactivity and properties of azetidine-containing molecules. Its unique structure and the presence of the Boc group make it an ideal candidate for probing the mechanisms of various chemical reactions and for developing new synthetic methodologies.
Used in Biochemical Applications:
In biochemical applications, 1-Boc-3-(Aminomethyl)azetidine may be used as a chiral auxiliary or ligand in asymmetric synthesis, taking advantage of its azetidine ring to induce selectivity in reactions. This can lead to the production of enantiomerically pure compounds, which are essential in the development of pharmaceuticals with fewer side effects and higher efficacy.
Used in the Production of Specialty Chemicals:
1-Boc-3-(Aminomethyl)azetidine is also used in the production of specialty chemicals, where its unique structural features can be exploited to create compounds with specific properties. These may include materials with tailored physical or chemical characteristics, such as solubility, stability, or reactivity, which are important in various industrial applications.

InChI:InChI=1/C9H18N2O2/c1-9(2,3)13-8(12)11-5-7(4-10)6-11/h7H,4-6,10H2,1-3H3

Upstream product

• 142253-54-1 tert-butyl 3-cyanoazetidine-1-carboxylate 
• 141699-58-3 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester 
• 141699-55-0 tert-butyl 3-hydroxyazetidine-1-carboxylate 

Downstream Products

• 1028286-25-0 3-(benzoylamino-methyl)-azetidine-1-carboxylic acid tert-butyl ester 
• 1026942-02-8 3-(benzenesulfonylamino-methyl)-azetidine-1-carboxylic acid tert-butyl ester 
• 1026576-25-9 3-[(cyclohexanecarbonyl-amino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester 
• 1201691-78-2 3-{[4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoylamino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester 
• 1173206-71-7 1-Boc-3-(aminomethyl)azetidine hydrochloride 
• 1575820-10-8 tert-butyl 3-[[(2-nitrophenyl)amino]methyl]-azetidine-1-carboxylate 

Relevant articles and documents

Cathepsin cysteine protease inhibitors

This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of Cathepsins K and L. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L

Compounds containing a 1-cyanopyrrolidinyl ring were identified as potent and reversible inhibitors of cathepsins K and L. The original lead compound 1 inhibits cathepsins K and L with IC50 values of 0.37 and 0.45 μM, respectively. Modification of compound 1 by replacement of the quinoline moiety led to the synthesis of N-(1-cyano-3-pyrrolidinyl)benzenesulfonamide (2). Compound 2 was found to be a potent inhibitor of cathepsins K and L with a Ki value of 50 nM for cathepsin K. Replacement of the 1-cyanopyrrolidine of compound 2 by a 1-cyanoazetidine increased the potency of the inhibitor by 10-fold. This increase in potency is probably due to an enhanced chemical reactivity of the compound toward the thiolate of the active site of the enzyme. This is demonstrated when the assay is performed in the presence of glutathione at pH 7.0 which favors the formation of a GSH thiolate anion. Under these assay conditions, there is a loss of potency in the 1-cyanoazetidine series due to the formation of an inactive complex between the GSH thiolate and the 1-cyanoazetidine inhibitors. 1-Cyanopyrrolidinyl inhibitors exhibited time-dependent inhibition which allowed us to determine the association and dissociation rate constants with human cathepsin K. The kinetic data obtained showed that the increase of potency observed between different 1-cyanopyrrolidinyl inhibitors is due to an increase of kon values and that the association of the compound with the enzyme fits an apparent one-step mechanism. 13C NMR experiments performed with the enzyme papain showed that compound 2 forms a covalent isothiourea ester adduct with the enzyme. As predicted by the kinetic analysis, the addition of the irreversible inhibitor E64 to the enzyme-cyanopyrrolidinyl complex totally abolished the signal of the isothiourea bond as observed by 13C NMR, thereby demonstrating that the formation of the covalent bond with the active site cysteine residue is reversible. Finally, compound 2 inhibits bone resorption in an in vitro assay involving rabbit osteoclasts and bovine bone with an IC50 value of 0.7 μM. 1-Cyanopyrrolidine represents a new class of nonpeptidic compounds that inhibit cathepsin K and L activity and proteolysis of bone collagen.