The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water.
(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro-acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times.
Huang
Ling
L
The Lab of Pharmaceutical Chemistry, School of Pharmaceutical Science, Sun Yat-Sen University, Guangzhou, China.
Liu
Juntao
J
Shan
Wenjun
W
Liu
Bao
B
Shi
Anding
A
Li
Xingshu
X
D000818:Animals; D002013:Bryozoa / Q000737:chemistry; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry; D015195:Drug Design; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000737:chemistry; D005559:Formamides / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D000068759:Formoterol Fumarate; D006859:Hydrogen / Q000737:chemistry*; D006865:Hydrogenation; D007700:Kinetics; D008956:Models, Chemical; D011092:Polyethylene Glycols / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
D003432:Cross-Linking Reagents; D004983:Ethanolamines; D005559:Formamides; D005561:Formates; D014867:Water; C030544:formic acid; D011092:Polyethylene Glycols; C031066:formamide; D006859:Hydrogen; D000068759:Formoterol Fumarate