NaBH4 in N-methylpyrrolidone: a safe alternative for hydride displacement reaction.
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.
Torisawa
Y
Y
Process Research Laboratory, Second Tokushima Factory, Otsuka Pharmaceutical Co. Ltd., Kawauchi-cho, 771-0182, Tokushima, Japan. torisawa@fact.otsuka.co.jp
Nishi
T
T
Minamikawa
J
J
D001894:Borohydrides / Q000737:chemistry; D001966:Bromine / Q000737:chemistry; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013723:Teratogens / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D001894:Borohydrides; D011760:Pyrrolidinones; D013723:Teratogens; C009282:sodium cyanoborohydride; C038678:N-methylpyrrolidone; D001966:Bromine