53144-56-2

Basic information

• Product Name: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol hydrochloride
• Synonyms: 1,3-Benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-, hydrochloride; 1,3-benzenediol, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-, hydrochloride (1:1); 5-(2-((1,1-Dimethylethyl)amino)-1-hydroxyethyl)-1,3-benzenediol hydrochloride; 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol hydrochloride (1:1)
• CAS NO: 53144-56-2
• Molecular Formula: C₁₂H₂₀ClNO₃
• Molecular Weight: 261.7451
• Mol File: 53144-56-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 419.2°C at 760 mmHg
• Flash Point: 165.3°C
• Vapor Pressure: 8.92E-08mmHg at 25°C
• CAS DataBase Reference: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol hydrochloride(53144-56-2)
• EPA Substance Registry System: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol hydrochloride(53144-56-2)

Safety Data

• Hazardous Substances Data: 53144-56-2(Hazardous Substances Data)

Upstream product

• 35086-59-0 1-(3',5'-diacetoxyphenyl)ethanone 
• 36763-39-0 3',5'-diacetyloxy-2-bromoacetophenone 
• 62932-92-7 2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one 
• 39878-43-8 2-chloro-1-(3,5-dihydroxy-phenyl)-ethanone 
• 37394-31-3 (-)-Terbutaline 
• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 28924-18-7 2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone 
• 103145-34-2 (R)-3’,5’-dibenzyloxyphenylbromohydrin 

Downstream Products

• 37394-31-3 (-)-Terbutaline 

Relevant articles and documents

Method for preparing levoterbutaline by using chiral prosthetic group

The invention discloses a method for preparing levoterbutaline by using a chiral prothetic group, the method comprises the following steps: taking S-(-)-tert-butyl sulfinamide as a raw material, and sequentially reacting with tert-butyl bromide and 3, 5-dibenzyloxy bromoacetophenone to obtain a compound 5; performing reduction reaction on the compound 5 under the catalysis of quaternary ammonium salt to obtain a compound 6; and removing the protection of tert-butyl sulfinyl from the compound 6 to obtain a compound 7, and carrying out hydrogenolysis on the compound 7 in an alcohol solvent in the presence of a palladium catalyst and hydrochloric acid to obtain the levoterbutaline. The method is simple and reliable, the preparation cost is low, and the ee of the chiral product is as high as 99.9%.

A method of preparing R-terbutaline

A method of preparing R-terbutaline is disclosed for the first time. According to the method, 3,5-dibenzyloxyacetophenone is adopted as an initial material, is subjected to a bromination reaction, and then reduced by borane-methyl sulfide complex under catalysis by S-methyl-CBS; a product is coupled with N-benzyl-tert-butylamine, and then is hydrogenated to remove benzyl to prepare optically pure R-terbutaline; and the R-terbutaline is salted by utilizing a corresponding acid to prepare a medical salt of the R-terbutaline.

Synthesis of the Adrenergic Bronchodilators (R)-Terbutalinel and (R)-Salbutamol from (R)-Cyanohydrins

Stereoselective syntheses of (R)-terbutaline and (R)-salbutamol acetal, which are important bronchodilators, starting from O-protected (R)-cyanohydrins are described. (R)-Terbutaline hydrochloride (R)-9·HCl is obtained in an overall yield of 44% with >98% ee from the O-bisallyl-protected cyanohydrin (R)-4k via a Ritter N-tertiary butylation to the amide (R)-6a, hydrogenation to the amino alcohol (R)-7a, and deprotection of the hydroxyl functions. (R)-Salbutamol acetals (R)-7b,c can be obtained from the corresponding O-protected (R)-cyanohydrins either via the route described for (R)-terbutaline or via selective hydrogenation of the protected cyanohydrin (R)-11 to the imino derivative, transimination with tert-butylamine, followed by hydrogenation with NaBH4 to give the 2-amino alcohol derivative (R)-12. Desilylation of (A)-12 to (R)-7c is performed with LiAlH4. Hydrolytic cleavage of the acetals (A)-7b and c to (R)-salbutamol was not yet possible without racemization.