213769-24-5Relevant academic research and scientific papers
Practical methods for the preparation of spiro[benzo[c]thiophene- 1(3H),4'-piperidine]-(2S)-oxide by resolution and asymmetric sulfoxidation
Nishi, Takahide,Nakajima, Katsuyoshi,Iio, Yukiko,Ishibashi, Koki,Fukazawa, Tetsuya
, p. 2567 - 2570 (1998)
We report simple and efficient methods for the preparation of enantiomerically pure spiro[benzo[c]thiophene-1(3H),4'-piperidine]-(2S)- oxide (S)-1, a key intermediate for the synthesis of tachykinin receptor antagonist, by resolution and asymmetric sulfoxidation. Racemic (RS)-1 can be resolved with (S)-(+)-mandelic acid in acetonitrile to give (S)-1 of >99% ee. We also describe the asymmetric sulfoxidation of sulfide 5 in excellent enantiomeric excess and high chemical yield by the use of the Davis reagent.
