Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol.
Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantioselectivity under mild reaction conditions.
Kamal
Ahmed
A
Biotransformation Laboratory, Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007. ahmedkamal@iict.res.in
Sandbhor
Mahendra
M
Ali Shaik
Ahmad
A
D008049:Lipase / Q000138:chemical synthesis*; D011433:Propranolol / Q000138:chemical synthesis*; D013015:Sotalol / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011433:Propranolol; D013015:Sotalol; D008049:Lipase