A practical preparation of 4,4-diphenylcyclohexanol: A key intermediate in the synthesis of MS-325

Synthetic Communications

Volumn 28, Issue 20, 1998, Pages 3895-3906

  Amedio Jr , John C ^a   Bernard, Paul J ^a   Fountain, Mark ^a   Van Wagenen Jr , Gerritt ^a  

^a EPIX Medical Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,4 DIPHENYLCYCLOHEXANOL; BENZOIN; CYCLOHEXANOL DERIVATIVE; GADOFOSVESET; GADOLINIUM CHELATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; THIN LAYER CHROMATOGRAPHY;

EID: 0031656194     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004943     Document Type: Article

References (20)

1. McMurry, T.J. et al PCT Publication WO 96/23526.
2. a) 4,4-Diphenylcyclohexanol has been found to be a metabolite of Pramiverine: Diekman, H.W.; Buehring, K.U.; Garbe, A. and Nowak, H. Arrzneim.-Forsch. 1976, 26(4B), 722-6.
3. b) The only other report found to reference 4,4-Diphenylcyclohexanol: German Patent #1793611 (1971).
4. Cost analysis was completed from published information by Aldrich, Fluka and Sigma Chemical. The availability of 3,4 and 5 were investigated through Chemcyclopedia.
5. Nomura, R; Matsuno, T. and Endo, T. J. Am. Chem. Soc. 1996, 118, 11666-11667.
6. Fukuzawa, S.; Tsuchimoto, T. and Kanai, T. Chemistry Lett. 1994, 1981-1984.
7. Mukaiyama, T.; Sato, T and Hanna, J. Chemistry Lett. 1973, 1041-1044.
8. Stinnett, J.W.; Vora, M.M. and Holy, N.L. Tetrahedron Lett. 1974, 3821-3824.
9. Kamochi, Y. and Kudo, T. Tetrahedron Lett. 1991, 3511-3514.
10. Tamami, B. and Lakouraj, M.M. Synth. Commun. 1995, 25(19), 3089-3096.
11. Mukherjee, D.K.; Palit, B.K. and Saha, C.R. J. Molecular Catalysis, 1994, 88, 57-70.
12. Zimmermann, H and Schuster, D.I. J. Am. Chem. Soc. 1962, 84, 4527-4540.
13. No decrease in purity was observed after one year at -5.0-0.0°C.
14. Zimmermann, H; Keese, R.; Nasielski, J. and Swenton, J.S. J. Am. Chem. Soc. 1966, 88, 4895-4904.
15. From reference 13: It was not reported if the 95% ethanol was anhydrous.
16. The remaining 5% is isopropanol.
17. The cost of 99.0% MVK was twice that for the 94.0% material (Aldrich Chemical).
18. 2 at 30 psi has been recently achieved by Mallinckrodt Medical chemists (S. Woulfe et al), St. Louis, Mo. (Unpublished results).
19. Hydrogenation of 4,4-diphenylcyclohex-2-ene-1-one to 4,4-diphenylcyclohexanone has been reported: Bunce, R.A.; Taylor, V.L. and Holt, E.M. J. Photochem. Photobiol. A: Chem. 1991, 57, 317-329. The ketone was isolated and fully characterized.
20. Frimer A.A. et al J. Org. Chem. 1989, 54, 4853-4866.