The addition of amines to diisobutylaluminum-imine complexes. Preparation of NPS R-568 hydrochloride

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3451-3454

  Barmore, Robert M ^a   Logan, Sarah R ^a   Van Wagenen, Bradford C ^a  

^a NPS Pharmaceutical Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; IMINE; N [3 (2 CHLOROPHENYL)PROPYL] 1 (3 METHOXYPHENYL)ETHYLAMINE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HYPERPARATHYROIDISM; POLYMERIZATION; PROTON TRANSPORT;

EID: 0032555026     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00603-0     Document Type: Article

References (12)

1. (a) Steffey, M.E.; Fox, J.; Van Wagenen, B.C.; Delmar, E.G.; Balandrin, M.F.; Nemeth, E.F. J. Bone Miner. Res. 1993, 8 (Suppl. 1), S175 (no. 236).
2. (b) Nemeth, E.F.; Van Wagenen, B.C.; Balandrin, M.F. PCT Intl. Appl. No. WO 93 04,373 (Chem. Abstr. 1993, 119, P 63054s).
3. (c) Van Wagenen, B.C.; Delmar, E.G.; Balandrin, M.F.; Steffey, M.E.; Nemeth, E.F. manuscript in preparation.
4. Van Wagenen, B.C.; D'Ambra, T.E. U.S. Patent 5,504,253, April 2, 1996.
5. Miller, A.E.G.; Biss, J.W.; Schwartzman, L.H. J. Organic Chem. 1959 24, 627-630.
6. (a) Marino, J.P.; Hurt, C.R. Synth. Commun. 1994, 24, 839-848.
7. (b) Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C.G. Tetrahedron: Asymmetry 1992, 3, 769-774.
8. (c) Zandbergen, P.; van den Nieuwendijk, A.M.C.H.; Brussee, J.; van der Gen, A., Kruse, C.G. Tetrahedron 1992, 48, 3977-3982.
9. Toluene and dichloromethane were found to give optimal results, little or no product was observed using either THF or heptane.
10. 3/MeOH yielded the product, 1 (1.25 g, 82%), as a clear, colorless oil.
11. l3C-NMR,and GC/MS. Each product has either successfully passed combustion analysis (Oneida Research Services, Inc.) or has been characterized by high-resolution mass spectrometry.
12. Enantiomeric purity was determined by chiral HPLC using a Chiralcel-OD HPLC column vs. a racemic standard prepared by the same method.