Improved syntheses of fluorinated tertiary butylamines

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3831-3834

  Ok, Dong ^a   Fisher, Michael H ^a   Wyvratt, Matthew J ^a   Meinke, Peter T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIMETHYL 2 FLUOROETHYLAMINE; 2 FLUORO 1 (FLUOROMETHYL) 1 METHYLETHYLAMINE; 2 FLUORO 1,1 BIS(FLUOROMETHYL)ETHYLAMINE; BUTYLAMINE; FLUORINE; ISOCYANIC ACID DERIVATIVE; MAGNESIUM DERIVATIVE; TERTIARY AMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; FLUORINATION; HYDROLYSIS; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033553362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00633-4     Document Type: Article

References (16)

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6. 3 as solvent, unless otherwise noted. Electrospray ionization LC/MS or electron impact GC/MS was used to verify monoisolopic molecular weights. All spectra were consistent with the assigned structures.
7. 7. For a review of cyclic sulfate chemistry, see Lohray, B. B. Synthesis 1992, 1035-1052.
8. 8. Nitrones readily undergo addition of organometallic reagents and other nucleophiles. See Chang, Z.-Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3464-3474 and 3475-3483 and references cited therein.
9. HF = 47.0 Hz); [m/z: 91.5 (M+H)+].
10. 10. White, G. J.; Garst, M. E. I. J. Org. Chem. 1991, 56, 3177-3178.
11. 2, 2H), 2.06 (br s, 1H), 1.25 (s, 6H). (c) The hydrochloride salt of 1 was prepared in quantitative yield from 11 according to the procedure described in 9e. However, more consistent results were obtained at 50 °C.
12. +].
13. 13. Ceruti, M.; Amisano, S.; Milla, P.; Viola, F.; Rocco, F.; Jung, M.; Cattel. L. J. Chem. Soc., Perkin Trans I 1995, 889-893.
14. HF = 46.0 Hz.); [m/z: 127.6 (M+H)+].
15. 15. Davis, F. A.; Reddy, G. V.; Bental, M.; Deutsch, C. J. Synthesis 1994, 701-702.
16. 16. Due to competitive removal of the TBS during the subsequent fluoride displacement reaction and the resulting production of side products, better results are obtained if the hydroxy phenethyl group is replaced with a simple benzyl protecting group.