Preparation of 3,4-fused-spiro[furan-5(5H),4′-piperidin]-2-one

Tetrahedron Letters

Volumn 50, Issue 37, 2009, Pages 5228-5230

  Liu, Jian ^a   Jian, Tianying ^a   Guo, Liangqin ^a   Atanasova, Tzvetomira ^a   Nargund, Ravi P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Iodolactonization; Spiro piperidine; Suzuki coupling

Indexed keywords

PIPERIDONE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; IODOLACTONIZATION REACTION; LACTONIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 67650909378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.035     Document Type: Article

References (14)

1. Patchett A.A., Nargund R.P., Tata J.R., Chen M.-H., Barakat K.J., Johnston D.B.R., Cheng K., Chan W.W.-S., Butler B., Hickey G., Jacks T., Schleim K., Pong S.-S., Chaung L.-Y.P., Chen H.Y., Frazier E., Leung K.H., Chiu S.-H.L., and Smith R.G. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 7001
2. Nargund R.P., Patchettt A.A., Bach M.A., Murphy M.G., and Smith R.G. J. Med. Chem. 41 (1998) 3103
3. Liu J., Jian T., Sebhat S., and Nargund R. Tetrahedron Lett. 47 (2006) 5115
4. Marxer A., Rodriguez H.R., McKenna J.M., and Tsai H.M. J. Org. Chem. 40 (1975) 1427
5. Parham W.E., Egberg D.C., Sayed Y.A., Traikill R.W., Keyser G.E., Neu N., Montgomery W.C., and Jones L. J. Org. Chem. 41 (1976) 2628
6. Sauter F., Stanetty P., Frohlich H., and Ramer W. Heterocycles 26 (1987) 2639
7. Sagara, T.; Itoh, S.; Nakashima, H.; Goto, Y.; Shimizu, A.; Iwasawa, Y.; Okamoto, O. PCT Int. Appl., WO2002088089, 2002.
8. Compound 5 was readily prepared from commercially available 2-hydroxy-6-methyl-nictinic acid by chlorination, esterification and conversion of 2-hydroxy to triflate:. Cale A.D., Gero T.W., Walker K.R., Lo Y.S., Welstead W.J., Jaques L.W., Johnson A.F., Leonard C.A., Nolan J.C., and Johnson D.N. J. Med. Chem. 32 (1989) 2178
9. Compound 6 was prepared following the literatures:. Eastwood P.R. Tetrahedron Lett. 41 (2000) 3705
10. Wustrow D.J., and Wise L.D. Syntheis (1991) 993
11. Mali R.S., and Patil S.R. Synth. Commun. 20 (1990) 167
12. Reich S.H., Melnick M., Pino M.J., Fuhry M.M., Trippe A.J., Appelt K., Davies J.F., Wu B.-W., and Musick L. J. Med. Chem. 39 (1996) 2781
13. 3, 125 MHz): δ 168.2, 165.8, 163.0, 153.9, 133.4, 132.2, 118.0, 84.8, 79.4, 40.3 (br), 39.8 (br), 33.4, 28.0, 23.4 ppm.
14. 3, 500 MHz) δ: 4.06 (2H, br), 3.21 (2H, br), 2.52 (4H, br), 2.46 (2H, br), 1.83 (2H, m), 1.58 (2H, d, J = 13.0 Hz), 1.46 (9H, s) ppm.