Integrated approach to the development and understanding of the borane reduction of a carboxylic acid

Organic Process Research and Development

Volumn 8, Issue 6, 2004, Pages 1072-1075

  Lobben, Paul C ^a   Leung, Simon Shun Wang ^a   Tummala, Srinivas ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; CARBOXYLIC ACID; REAGENT;

ADDITION REACTION; CALORIMETRY; CONFERENCE PAPER; COOLING; FLOWMETER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; KINETICS; MEDICAL RECORD; REDUCTION;

EID: 10044239412     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049910h     Document Type: Conference Paper

References (15)

1. Nicolai, E.; Teulon, J.-M. Diarylmethylidenefuran Derivatives and Their Uses in Therapeutics. U.S. Patent 5,807,873, September 15, 1998.
2. Wann, S. R.; Thorsen, P. T.; Kreevoy, M. M. J. Org. Chem. 1981, 46, 2579-2581.
3. Various reagents and techniques have been employed to address the issue of reactivity and chemoselectivity. For lead references for the selective reduction of carboxyl-containing molecules, please see: (a) Seyden-Penne, J. Reductions by the Alumina- and Borohydrides in Organic Synthesis, 2nd ed; Wiley-VCH: New York, 1997. (b) Abdel-Magid, A. F., Ed. Reductions in Organic Synthesis; Recent Advances and Practical Applications; American Chemical Society: Washington, D.C, 1996. (c) Barrett, A. G. M. Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M., Ed.; Pergamon Press: New York, 1991; pp 235-257.
4. Various reagents and techniques have been employed to address the issue of reactivity and chemoselectivity. For lead references for the selective reduction of carboxyl-containing molecules, please see: (a) Seyden-Penne, J. Reductions by the Alumina- and Borohydrides in Organic Synthesis, 2nd ed; Wiley-VCH: New York, 1997. (b) Abdel-Magid, A. F., Ed. Reductions in Organic Synthesis; Recent Advances and Practical Applications; American Chemical Society: Washington, D.C, 1996. (c) Barrett, A. G. M. Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M., Ed.; Pergamon Press: New York, 1991; pp 235-257.
5. Various reagents and techniques have been employed to address the issue of reactivity and chemoselectivity. For lead references for the selective reduction of carboxyl-containing molecules, please see: (a) Seyden-Penne, J. Reductions by the Alumina- and Borohydrides in Organic Synthesis, 2nd ed; Wiley-VCH: New York, 1997. (b) Abdel-Magid, A. F., Ed. Reductions in Organic Synthesis; Recent Advances and Practical Applications; American Chemical Society: Washington, D.C, 1996. (c) Barrett, A. G. M. Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines. In Comprehensive Organic Synthesis, Vol. 8; Trost, B. M., Ed.; Pergamon Press: New York, 1991; pp 235-257.
6. 3·THF in a 400 L cylinder, please see Chem. Eng. News, July 1, 2002 and Safety Highlights in Org. Process Res. Dev. 2003, 7, 1029-1033.
7. 3·THF in a 400 L cylinder, please see Chem. Eng. News, July 1, 2002 and Safety Highlights in Org. Process Res. Dev. 2003, 7, 1029-1033.
8. 3·THF in a 400 L cylinder, please see Chem. Eng. News, July 1, 2002 and Safety Highlights in Org. Process Res. Dev. 2003, 7, 1029-1033.
9. 4, MSA, and DME used in the early process, when capital and labor expenses are considered, the cost is comparable. However, the true savings with the current process are realized when evaluating the processing and environmental aspects.
10. See the Supporting Information for a schematic diagram of the integrated reactor.
11. (a) Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786-2792.
12. (b) Brown, H. C.; Stocky, T. P. J. Am. Chem. Soc. 1977, 99, 8218-8226.
13. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proced. Int. 1985, 17, 317-384.
14. Lappert, M. F. J. Chem. Soc. 1958, 2790.
15. The reaction rate is dependent on the concentration and temperature of the reaction mixture as well as the equivalents of reagent.