Efficient and general asymmetric syntheses of (R)-chroman-4-amine salts

Tetrahedron Letters

Volumn 51, Issue 45, 2010, Pages 5904-5907

  Voight, Eric A ^a   Daanen, Jerome F ^a   Hannick, Steven M ^a   Shelat, Bhadra H ^a   Kerdesky, Francis A ^b   Plata, Daniel J ^b   Kort, Michael E ^a  

^a ABBOTT LABORATORIES   (United States)

^b Process Research and Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CHROMAN DERIVATIVE; MANDELIC ACID; TARTARIC ACID;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION;

EID: 77957789979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.006     Document Type: Article

References (20)

1. J. Lloyd, K.S. Atwal, H.J. Finlay, M. Nyman, T. Huynh, R. Bhandaru, A. Kover, J. Schmidt, W. Vaccaro, M.L. Conder, T. Jenkins-West, and P. Levesque Bioorg. Med. Chem. Lett. 17 2007 3271
2. K. Biswas, A. Li, J.J. Chen, D.C. D'Amico, C. Fotsch, N. Han, J. Human, Q. Liu, M.H. Norman, B. Riahi, C. Yuan, H. Suzuki, D.A. Mareska, J. Zhan, D.E. Clarke, A. Toro, R.D. Groneberg, L.E. Burgess, D. Lester-Zeiner, G. Biddlecome, B.H. Manning, L. Arik, H. Dong, M. Huang, A. Kamassah, R. Loeloff, H. Sun, F. Hsieh, G. Kumar, G.Y. Ng, R.W. Hungate, B.C. Askew, and E. Johnson J. Med. Chem. 50 2007 2200 2212
3. Chroman-4-ones 8, 14-20, and 25-29 were either commercially available or prepared from the corresponding 2-hydroxyacetophenone and dialkyl ketone in pyrrolidine and MeOH: H.J. Kabbe Synthesis 1978 886 887
4. All 2-hydroxyacetophenones were either commercially available or prepared according to: Uchida, H.; Kosuga, N.; Satoh, T.; Hotta, D.; Kamino, T.; Maeda, Y.; Amano, K.; Akada, Y. PCT Int. Appl. WO2007010383, 2007.
5. E. Marzi, and M. Schlosser Tetrahedron 61 2005 3393 3401
6. Chroman-4-one 31 was prepared from 3-(trifluoromethoxy)phenol according to: F. Camps, J. Coll, A. Messeguer, M.A. Pericas, and S. Ricart Synthesis 1980 725 727
7. K. Huang, F.G. Merced, M. Ortiz-Marciales, H.J. Meléndez, W. Correa, and M. De Jesús J. Org. Chem. 73 2008 4017 4026
8. K. Han, J. Park, and M.-J. Kim J. Org. Chem. 73 2008 4302 4304
9. M.-J. Kim, W.-H. Kim, K. Han, Y.K. Choi, and J. Park Org. Lett. 9 2007 1157 1159
10. M.J. Burk, M.W. Wang, and J.R. Lee J. Am. Chem. Soc. 118 1996 5142 5143
11. Hydrogenation of enamide 31 provided efficient conversion to amide 32 with 83% ee. (Ligand = (R)-1-[(S)-(di-tert-butylphosphino)ferrocenyl] ethyldiphenylphosphine).
12. A. Burgard, H.-J. Lang, and U. Gerlach Tetrahedron 55 1999 7555 7562
13. E.J. Corey, R.K. Bakshi, S. Shibata, C.-P. Chen, and V.K. Singh J. Am. Chem. Soc. 109 1987 7925 7926
14. C.E. Garrett, K. Prasad, O. Repič, and T.J. Blacklock Tetrahedron: Asymmetry 13 2002 1347 1349
15. N,N-Diethylaniline borane has been employed previously as a chroman-4-one stoichiometric reducing agent using the B-Me CBS catalyst with lower ee: I. Bichlmaier, A. Siiskonen, M. Finel, and J. Yli-Kauhaluoma J. Med. Chem. 49 2006 1818 1827
16. 4), filtered, and concentrated, to provide (S)-chroman-4-ol 9 (17.4 g, 89.0 mmol). Analysis by analytical chiral HPLC (Chiralcel OJ 4.6 × 25 mm, 20% isopropanol/hexane, 23 °C, 0.5 mL/min) showed 99% ee versus a racemic reference.
17. +.
18. Gharat, L. A.; Joshi, U. M.; Joshi, N. K. PCT Int. Appl. WO 2007/042906, 2007.
19. For example, see Ref. 2.
20. +.