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Paper | Regular issue | Vol 38, No. 8, 1994, pp.1889-1896
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6758
EPC-Synthesis of (S)-3-Hydroxy-3-mercaptomethylquinuclidine, a Chiral Building Block for the Synthesis of the Muscarinic Agonist AF 102B

Michael Bös* and Rolf Canesso

*Pharma Division, Pharma Preclinical Research & Development, F.Hoffmann-La Roche Ltd., Grenzacherstrasse 124, CH-4070 Basel, Switzerland


The catalytic modification of the Sharpless-epoxidation reaction was employed in a short EPC-synthesis of the title compound. The asymmetric epoxidation of the allylic alcohol (6) proceeded in 75 % yield and 94 % enantiomeric excess. In a 4 step sequence the epoxide (7) was transformed to (S)-3-hydroxy-3-mercaptomethylquinuclidine (11).