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NaBH4 in N-methylpyrrolidone: a safe alternative for hydride displacement reaction
Y Torisawa1, T Nishi, J Minamikawa
1Process Research Laboratory, Second Tokushima Factory, Otsuka Pharmaceutical Co. Ltd., Kawauchi-cho, 771-0182, Tokushima, Japan. torisawa@fact.otsuka.co.jp
Bioorganic & Medicinal Chemistry Letters
|October 10, 2001
Abstract:
Enhanced reactivity of NaBH4 was observed as a solution in N-methylpyrrolidone (NMP). Thus, a simple protocol for debromination of alkyl bromide and sulfonate is devised with NMP as a key solvent. Also described is a new mixed borohydride system, NaBH4-LiOTf-NMP, which works as an alternative to NaBH3CN for the SN2 type displacement. No reports have ever revealed usefulness of NMP in borohydride reduction.