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Asymmetric Synthesis of ( R )‐Fluoxetine: A Practical Approach Using Recyclable and in‐situ Generated Oxazaborolidine Catalyst
Author(s) -
PADIYA Kamlesh,
GAGARE Pravin,
GAGARE Manjiri,
LAL Bansi
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990190
Subject(s) - chemistry , yield (engineering) , in situ , catalysis , key (lock) , enantioselective synthesis , combinatorial chemistry , organic chemistry , ecology , metallurgy , materials science , biology
A practical route for the synthesis of ( R )‐fluoxetine·HCl ( ee =96%) in 56% overall yield was described. The key intermediate ( R )‐3‐chloro‐1‐phenyl‐1‐propanol was obtained by the asymmetric reduction of prochiral 3‐chloropropiophenone using in‐situ generated oxazaborolidine catalyst derived from ( S )‐ α , α ‐diphenylprolinol. The chiral procatalyst ( S )‐ α , α ‐diphenylprolinol was recovered quantitatively and recycled. An improved practical synthesis of ( S )‐ α , α ‐diphenylprolinol was also discussed.