Methylborohydride, lithium

That means that this method is a neat little way one can get the ever lovely MDEA (Methylenedioxyethyl amphetamine, the softer cousin of X). Strike hears you asking So if one uses lithium tri-methylborohydride can one get methamphetamine out of that nitro group . Good question. Unfortunately the answer is no. The authors say Interestingly, N-alkylated products were not produced when other alkylborohydrides were used." Fair enough. Here s the recipe ... 

Prepared from lithium methylborohydride and HC1 Brown Cole Srebnik Kim J. Org. Chem. 1986,51. 4925. Srebnik Cole Brown Tetrahedron Lett. 1987, 28. 3771, J. Org. Chem. 1990, 55, 5051. 

Another route to tertiary alcohols involves monomethylborane (MeBH2), which can be prepared from lithium methylborohydride (LiMeBH3). 3l Reaction of MeBH2 with 2 equivalents of 1-hexene gave 185. Carbonylation and oxidation gave a 1 1 mixture of 186 and 187.131 When 10 equivalents of 1-hexene were used and the hydroboration was done at -25°C (in THF), carbonylation and oxidation gave 186 in 96% yield. 31 Ketones rather than alcohols can be synthesized if the carbonylation step is done in the presence of... 

The easily prepared, stable solid reagent diphenylamine-borane (Ph2NH BH8) has been shown to be more reactive than aliphatic amine-boranes and almost as reactive as borane-THF for the reduction of ketones acids are also reduced to alcohols. Polyethylene glycols (PEG) catalyse the reduction of ketones by sodium borohydride under phase-transfer (PT) conditions, for example in solid-liquid PT with PEG as solvent. The solid zinc borohydride-dimethylformamide complex reduces aldehydes and ketones to alcohols, but only one hydrogen atom from each tetrahydridoborate unit is utilized. The different rates of reduction of various classes of ketone (saturated aliphatic faster than aromatic, and a -unsaturated very slow) suggest a possible selectivity between ketones. The corresponding cadmium complex, prepared in situ, reacts similarly. Lithium methylborohydride, LiMeBHj, prepared as shown in equation (1), where... 

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