Synthesis of Cinacalcet congeners

Tetrahedron Letters

Volumn 45, Issue 45, 2004, Pages 8355-8358

  Wang, Xin ^a   Chen, Ying ^a   Crockett, Richard ^a   Briones, Jorge ^a   Yan, Tony ^a   Orihuela, Carlos ^a   Zhi, Benxin ^a   Ng, John ^a  

^a AMGEN INC   (United States)

Author keywords

Cinacalcet; Dihydronaphthalene; Double bond migration

Indexed keywords

CINACALCET;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 5144220617     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.063     Document Type: Article

References (12)

1. Cinacalcet HCl is an oral calcimimetic drug, first in class agent for the treatment of hyperparathyroidism and the preservation of bone density in patients with kidney failure or hypercalcemia due to cancer. Cinacalcet received the FDA approval on March 8, 2004. N. Franceschini, M.S. Joy, and A. Kshirsagar Expert Opin. Invest. Drugs 12 2003 1413
2. 5-Hydroxy-1-tetralone was purchased from Aldrich at 5 g/$124.40.
3. E.M. Vogl, and S.L. Buchwald J. Org. Chem. 67 2002 106
4. The crude triflate 7 is not suitable for the next step and needs purification before use.
5. I. Pendrak, and P.A. Chambers J. Org. Chem. 60 1995 3249
6. B.I. Cruikshank, and N.R. Davies Aust. J. Chem. 26 1973 1935 Olefin isomerization can also be catalyzed by other transition metals
7. 3): 22.3, 28.1, 29.9, 125.6, 127.1, 127.3, 127.9, 129.5, 135.3, 135.7, 138.2, 202.1.
8. 3): 143.5, 140.9, 140.6, 136.5, 132.2, 131.7, 129.7, 129.0, 127.3, 126.5, 124.0, 125.5, 123.9, 123.0, 53.6, 47.5, 33.8, 32.2, 28.9, 23.8, 23.0.
9. For a recent example utilizing a CBS reduction of a ketone on a kilogram scale, see: J. Duquette, M. Zhang, L. Zhu, and R.S. Reeves Org. Process Res. Dev. 7 2003 285
10. A.S. Thompson, G.R. Humphrey, A.M. Demarco, D.J. Mathre, and E.J.J. Grabowski J. Org. Chem. 58 1993 5886
11. Enantiomeric excess of all the relevant compounds was determined by chiral HPLC. Two types of chiral columns were used: OD-H 250 × 4.6 mm or OJ-H 250 × 4.6 mm; mobile phase = hexane/IPA 90/10 or 95/5 (v:v); flow rate = 0.5 mL/min; wavelength = 260 nm; column temperature = ambient
12. The aldehyde 20 is prepared by the following scheme in good yield: Equation Presented.