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Paper | Regular issue | Vol 78, No. 7, 2009, pp.1777-1786
Published online, 13th March, 2009
DOI: 10.3987/COM-09-11677
Reaction of 1-Azabicyclo[1.1.0]butane with Activated Amides

Kazuhiko Hayashi,* Eiko Kujime, Hajime Katayama, Shigeki Sano, and Yoshimitsu Nagao

*College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Moriyama-ku, Nagoya 463-8521, Japan

Abstract

1-Azabicyclo[1.1.0]butane (ABB, 1) reacted with 3-acyl-1,3-thiazolidine-2-thiones (7,11am) in the presence of a catalytic amount of Mg(OTf)2 to give the corresponding 2-(1-acylazetidin-3-yl)thio-1,3-thiazolines (8,12am). It was hypothesized that this reaction is primarily influenced by a steric bulkiness of acyl groups in 3-acyl-1,3-thiazolidine-2-thiones. Resulting compounds (8, 12k) were readily converted to thiols (13,14), and azetidine-3-thiol hydrochloride (15), which is the key intermediate of 1-(1,3-thiazolin-2-yl)azetidine-3-thiol hydrochloride (4) useful for the preparation of a new oral 1β-methylcarbapenem antibiotic L-084, was obtained quantitatively by hydrolysis of 14.