Reductive Amination of γ-Keto Mono or Geminal Bisphosphonates with Primary Amines

Kang-Yeoun Jung; Mi-Young Lee

Journal of Industrial and Engineering Chemistry, Vol.5, No.3, 224-227, September, 1999

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Reductive Amination of γ-Keto Mono or Geminal Bisphosphonates with Primary Amines

Kang-Yeoun Jung^†, and Mi-Young Lee

Department of Industrial Chemistry, Kangnung National University, Kanhnung, Kangwondo 210-702, Korea

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Reductive amination of carbonyl functionality to an amine is a very important tool in the synthesis of different kinds of amines. Commonly most of these processes have been applied tor the carbonyl compounds, which contain various substituents except phosphonate functional group to an amine. During our study to synthesize aminated nomo or bisphosphonate compounds as a drug we have tried several methods for the reductive amination of γ-Keto mono or bisphosphonates. To get the desired product in a reasonable yield we have used, among various methods, the one-pot reductive amination process using sodium triacetoxyborohydride and acetic acid.

Keywords:bisphosphonates;reductive amination;triacetoxyborohydride

[References]

Anne M, Chollet G, Liliane VQ, Yen VQ, Francois LG, Synth. Commun., 21, 1847 (1991)
Brindaban CR, Adinath M, Arunkanti S, J. Org. Chem., 63, 370 (1998)
Emerson WS, Org. React., 4, 174 (1948)
Johnson HE, Crosby DG, AAPG Bull., 27, 2205 (1962)
Borch RF, Bernstein MD, Durst HD, J. Am. Chem. Soc., 93, 2897 (1971)
Brindaban CR, Adinath M, Arunkanti S, J. Org. Chem., 63, 370 (1998)
Walter JG, Francis A, J. Am. Chem. Soc., 82, 6078 (1960)
Yoon NM, Kim EG, Son HS, Choi J, J. Synth. Commun., 23, 1595 (1993)
Sim TB, Choi JS, Joung JM, Yoon NM, J. Org. Chem., 62, 2357 (1997)
Ahmed FA, Kenneth GC, Bruce DH, Cynthia AM, Rekha DS, AAPG Bull., 61, 3849 (1996)
Anne M, Chollet G, Liliane VQ, Yen VQ, Francois LG, Synth. Commun., 21, 1847 (1991)
Priyadarshanie B, Yannick L, Liliana PR, Denis P, Valery W, J. Org. Chem., 62, 1630 (1997)
Cynthia KM, Jung KY, J. Org. Chem., 56, 867 (1991)
Cynthia KM, Jung KY, J. Org. Chem., 56, 2326 (1991)
Cynthia KM, Jung KY, Grote WC, Hansen K, Phosphorus Sulfur Silicon, 75, 23 (1993)
Darmstadt E, Dyeing Reagents for Thin Layer and Paper Chromatography, Federal Republic of Germany (1978)
Springer V, Thin-Layer Chromatography, New York and London, 2nd Ed. (1969)

[Referenced By]

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[1] Anne M, Chollet G, Liliane VQ, Yen VQ, Francois LG, Synth. Commun., 21, 1847 (1991)

[2] Brindaban CR, Adinath M, Arunkanti S, J. Org. Chem., 63, 370 (1998)

[3] Emerson WS, Org. React., 4, 174 (1948)

[4] Johnson HE, Crosby DG, AAPG Bull., 27, 2205 (1962)

[5] Borch RF, Bernstein MD, Durst HD, J. Am. Chem. Soc., 93, 2897 (1971)

[6] Brindaban CR, Adinath M, Arunkanti S, J. Org. Chem., 63, 370 (1998)

[7] Walter JG, Francis A, J. Am. Chem. Soc., 82, 6078 (1960)

[8] Yoon NM, Kim EG, Son HS, Choi J, J. Synth. Commun., 23, 1595 (1993)

[9] Sim TB, Choi JS, Joung JM, Yoon NM, J. Org. Chem., 62, 2357 (1997)

[10] Ahmed FA, Kenneth GC, Bruce DH, Cynthia AM, Rekha DS, AAPG Bull., 61, 3849 (1996)

[11] Anne M, Chollet G, Liliane VQ, Yen VQ, Francois LG, Synth. Commun., 21, 1847 (1991)

[12] Priyadarshanie B, Yannick L, Liliana PR, Denis P, Valery W, J. Org. Chem., 62, 1630 (1997)

[13] Cynthia KM, Jung KY, J. Org. Chem., 56, 867 (1991)

[14] Cynthia KM, Jung KY, J. Org. Chem., 56, 2326 (1991)

[15] Cynthia KM, Jung KY, Grote WC, Hansen K, Phosphorus Sulfur Silicon, 75, 23 (1993)

[16] Darmstadt E, Dyeing Reagents for Thin Layer and Paper Chromatography, Federal Republic of Germany (1978)

[17] Springer V, Thin-Layer Chromatography, New York and London, 2nd Ed. (1969)