Broxaterol

Broxaterol
Names
	IUPAC name 1-(3-Bromo-5-isoxazolyl)-2-(tert-butylamino)ethanol
Identifiers
CAS Number	76596-57-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2105475 ;
ChemSpider	64294 ;
ECHA InfoCard	100.071.338
MeSH	Broxaterol
PubChem CID	71149;
UNII	ZE4IRB4DUC ;
CompTox Dashboard (EPA)	DTXSID20868402 ;
	InChI InChI=1S/C9H15BrN2O2/c1-9(2,3)11-5-6(13)7-4-8(10)12-14-7/h4,6,11,13H,5H2,1-3H3 Key: JBRBWHCVRGURBA-UHFFFAOYSA-N ; InChI=1/C9H15BrN2O2/c1-9(2,3)11-5-6(13)7-4-8(10)12-14-7/h4,6,11,13H,5H2,1-3H3 Key: JBRBWHCVRGURBA-UHFFFAOYAK;
	SMILES CC(C)(C)NCC(C1=CC(=NO1)Br)O;
Properties
Chemical formula	C9H15BrN2O2
Molar mass	263.135 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Broxaterol is a β₂ adrenoreceptor agonist.^[1] It is part of a class of drugs that affect the smooth muscle receptors in the body, often in use cases for respiratory disease that respond to this type of treatment.

Synthesis

The 1,3-dipolar cycloaddition between bromonitrile oxide, produced in situ from dibromoformaldoxime, and 3-butyn-2-one gives a mixture of isoxazoles, mainly the isomer shown required for broxaterol. Selective α-bromination of the acetyl group with pyridinium tribromide gives a bromoketone whose carbonyl group is reduced with sodium borohydride to produce a bromoethanol derivative. Treatment of this with tert-butylamine yields broxaterol.^[2]^[3]^[4]^[5]

References

^ Nava S, Crotti P, Gurrieri G, Fracchia C, Rampulla C (January 1992). "Effect of a beta 2-agonist (broxaterol) on respiratory muscle strength and endurance in patients with COPD with irreversible airway obstruction". Chest. 101 (1): 133–40. doi:10.1378/chest.101.1.133. PMID 1345900. Archived from the original on 2013-04-14.
^ US patent 4276299, Davide Della Bella and Dario Chiarino, "1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol", issued 1981-06-30, assigned to Zambon SpA
^ De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Spezia, Sandro (1989). "Chemoenzymatic synthesis of chiral isoxazole derivatives". The Journal of Organic Chemistry. 54 (11): 2646–2650. doi:10.1021/jo00272a037.
^ Rohloff, John C.; Robinson, James; Gardner, John O. (1992). "Bromonitrile oxide [3+2] cycloadditions in water". Tetrahedron Letters. 33 (22): 3113–3116. doi:10.1016/S0040-4039(00)79827-3.
^ Battilocchio, Claudio; Bosica, Francesco; Rowe, Sam M.; et al. (2017). "Continuous Preparation and Use of Dibromoformaldoxime as a Reactive Intermediate for the Synthesis of 3-Bromoisoxazolines". Organic Process Research & Development. 21 (10): 1588–1594. doi:10.1021/acs.oprd.7b00229.

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[pmid1345900-1] Nava S, Crotti P, Gurrieri G, Fracchia C, Rampulla C (January 1992). "Effect of a beta 2-agonist (broxaterol) on respiratory muscle strength and endurance in patients with COPD with irreversible airway obstruction". Chest. 101 (1): 133–40. doi:10.1378/chest.101.1.133. PMID 1345900. Archived from the original on 2013-04-14.

[2] US patent 4276299, Davide Della Bella and Dario Chiarino, "1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol", issued 1981-06-30, assigned to Zambon SpA

[3] De Amici, Marco; De Micheli, Carlo; Carrea, Giacomo; Spezia, Sandro (1989). "Chemoenzymatic synthesis of chiral isoxazole derivatives". The Journal of Organic Chemistry. 54 (11): 2646–2650. doi:10.1021/jo00272a037.

[4] Rohloff, John C.; Robinson, James; Gardner, John O. (1992). "Bromonitrile oxide [3+2] cycloadditions in water". Tetrahedron Letters. 33 (22): 3113–3116. doi:10.1016/S0040-4039(00)79827-3.

[5] Battilocchio, Claudio; Bosica, Francesco; Rowe, Sam M.; et al. (2017). "Continuous Preparation and Use of Dibromoformaldoxime as a Reactive Intermediate for the Synthesis of 3-Bromoisoxazolines". Organic Process Research & Development. 21 (10): 1588–1594. doi:10.1021/acs.oprd.7b00229.

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