Chemo-enzymatic synthesis of the antidepressant duloxetine and its enantiomer

Sodium borohydride reduction of 3‐chloro‐1‐(2‐thienyl)‐1‐propanone gave the corresponding racemic alcohol which was kinetically resolved with lipase B from Candida antarctica as catalyst to yield the chiral building blocks (S)‐3‐chloro‐1‐(2‐thienyl)‐1‐propanol and the corresponding (R)‐butanoate. Th...

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Veröffentlicht in:	Chirality (New York, N.Y.) N.Y.), 2000, Vol.12 (1), p.26-29
Hauptverfasser:	Liu, Huiling, Hoff, Bård Helge, Anthonsen, Thorleif
Format:	Artikel
Sprache:	eng
Schlagworte:	antidepressant Antidepressive Agents - chemical synthesis Antidepressive Agents - isolation & purification Candida - enzymology Duloxetine Duloxetine Hydrochloride kinetic resolution Kinetics Lipase - metabolism lipase catalysis Saccharomyces cerevisiae - enzymology Stereoisomerism stereospecificity Thiophenes - chemical synthesis Thiophenes - isolation & purification
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Beschreibung
Zusammenfassung:	Sodium borohydride reduction of 3‐chloro‐1‐(2‐thienyl)‐1‐propanone gave the corresponding racemic alcohol which was kinetically resolved with lipase B from Candida antarctica as catalyst to yield the chiral building blocks (S)‐3‐chloro‐1‐(2‐thienyl)‐1‐propanol and the corresponding (R)‐butanoate. The enantiopure chiral building blocks were converted into Duloxetine and its enantiomer. Chirality 12:26–29, 2000. © 2000 Wiley‐Liss, Inc.
ISSN:	0899-0042 1520-636X
DOI:	10.1002/(SICI)1520-636X(2000)12:1<26::AID-CHIR5>3.0.CO;2-Z