188730-96-3

Upstream product

• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 299964-35-5 (+/-)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 
• 299964-37-7 Acetic acid (S)-1-(4-benzyloxy-3-nitro-phenyl)-2-bromo-ethyl ester 
• 188690-82-6 (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 
• 193761-53-4 (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol 

Downstream Products

• 289657-25-6 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol 
• 67346-49-0 (S,S)-formoterol 
• 67346-50-3 (S,R)-Formoterol 

Relevant academic research and scientific papers

Asymmetric transfer hydrogenation of ketones catalyzed by hydrophobic metal-amido complexes in aqueous micelles and vesicles

Asymmetric transfer hydrogenation of ketones, especially α-bromomethyl aromatic ketones, catalyzed by unmodified, hydrophobic transition metal-amido complexes (TsDPEN-M), was performed successfully with significant enhancement of activity, chemoselectivity, and enantio-selectivity (up to 99% ee) in aqueous media containing micelles and vesicles. The hydrophobic catalyst, embedded in micelles constructed from the surfactant cetyltrimethylammonium bromide (CTAB), could be separated from the organic phase along with the products and was recycled for at least six times.

An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases

The potent β2-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. Copyright (C) 2000 Elsevier Science Ltd.

Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents.