ChemicalBook CAS DataBase List Olodaterol

Olodaterol synthesis

2synthesis methods

Product Name:Olodaterol
CAS Number:868049-49-4
Molecular formula:C21H26N2O5
Molecular Weight:386.44

Olodaterol, also known as BI 1744, is a long acting beta-adrenoceptor agonist used as an inhalation for treating patients with chronic obstructive pulmonary disease (COPD), manufactured by Boehringer-Ingelheim. Olodaterol was approved by FDA in 2014 for the treatment of chronic obstructive pulmonary disease.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

Bouyssou, Thierry; Hoenke, Christoph; Rudolf, Klaus; Lustenberger, Philipp; Pestel, Sabine; Sieger, Peter; Lotz, Ralf; Heine, Claudia; Buettner, Frank H.; Schnapp, Andreas; Konetzki, Ingo. Discovery of olodaterol, a novel inhaled β2-adrenoceptor agonist with a 24h bronchodilatory efficacy. Bioorganic & Medicinal Chemistry Letters. Volume 20. Issue 4. Pages 1410-1414. Journal. (2010).

869478-13-7 Synthesis

8-[(1R)-1-Hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one

869478-13-7
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868049-49-4
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$56.00/1 mg

Yield:868049-49-4 99.27%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 50; under 2250.23 Torr;

Steps:

1.3 3) Preparation of crude odastatol hydrochloride
60 g (0.117 mol) prepared in the step 2) 6-Benzyloxy-8-{(R)-1-hydroxy-2-[2-(4-methoxy-phenyl)- 1,1-Dimethyl-ethylamino]-ethyl}-4H-benzo[1,4]oxazin-3-one, 600 ml of methanol and 8 g of 10% palladium on carbon were added to the reaction flask and heated to 50 ° C. , hydrogenation under 3 bar of hydrogen pressure. Then, the catalyst was removed by suction filtration, and the solvent was evaporated to dryness to dryness to give 49.1 g of white foamy solid, yield: 99.27%. Purity: 95.3%.

References:

Shanghai Fangyu Health Pharmaceutical Technology Co., Ltd.;Yu Xiong;Zhang Yuanwei;Yuan Xilun CN109096218, 2018, A Location in patent:Paragraph 0074; 0079-0080

FullText

6-benzyloxy-8-((R)-2-chloro-1-hydroxy-ethyl)-4H-benzo[1,4]-oxazin-3-one

869478-11-5
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868049-49-4
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$56.00/1 mg

References

Olodaterol Related Search:

Ethyl-3-Amino-2-[(2'-Cyanoiphenyl-4-yl) Methyl]-Amino Benzoate Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (Z)-Methyl 2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d] iMidazole-4-carboxylate