Practical chemoenzymic synthesis of both enantiomers of propranolol

Optimizing lipase activity, enantioselectivity, and stability with medium engineering and immobilization for ?-blocker synthesis

“…The substrate (±)1-chloro-2-acetoxy-3(1-naphthyloxy)-propane was prepared by the method described by Bevinakatti and Banerji (1991). 1-Naphthol, epichlorohydrin, acetyl chloride, acetone, dimethylsulfoxide (DMSO), 1,4-dioxane, dimethyl formamide (DMF), 1-propanol, and tetrahydrofuran (THF) were purchased from Aldrich Chemical Co. (Milwaukee, WI).…”

Combination of Vitamin E with a Carotenoid:α-Tocopherol and Trolox Linked toβ-Apo-8′-carotenoic Acid

“…[71] No reaction was observed with amines as a base. [72] With preformed Na-tocopherolate, only minor amounts of the glycidyl ether 9 were formed. [73] Ring opening to the glycerol ether 10 was achieved with dilute sulfuric acid, while basic conditions failed.…”

An efficient chiral synthesis of (R)-N-[3-acetyl-4-(2-hydroxy-3-isopropylamino-propoxy)phenyl]-butanamide with high enantioselectivity

“…These aryloxypropanolamine derivatives are always cardioselective and the S-enantiomers are generally 50-500 times more effective than the R-enantiomers in their β-blocking activity. To date, several documents have reported the asymmetric synthesis of these compounds, such as atenolol [14,15] , propranolol [16,17] and the title compound acebutolol [18] . Reported methods related to asymmetric resolution of the corresponding racemates, asymmetric lipase-catalyzed kinetic resolution or chiral pool methods, which possess many disadvantages, such as high costs, multiple steps, low overall yields and low optical purity.…”