Amine To amide

R4N= BnEtsN or BU4N Heterocylces 1980, 14, 1437, 1441 reduction of amides to amines reduction of nitriles to amines... 

Reduction of Carboxylic Acids to Alcohols. In addition to the nonsupported catalysts mentioned for the hydrogenation of amides to amines, mthenium and rhenium on alumina can be used to reduce carboxyHc acids to alcohols. The conditions for this reduction are somewhat more severe than for most other hydrogenation reactions and require higher temperatures, >150° C, and pressures, >5 MPa (725 psi) (55). Various solvents can be used including water. 

HOFMANN Amide Degradation Degradation o( amides to amines by means of hypohaiides... 

Borane and sodium in 1-propanol are good reducing agents for all three types of amides. Another reagent that reduces disubstituted amides to amines is trichloro-... 

Scheme 46 Fe-catalyzed reduction of amides to amines under either thermal or photoassisted conditions...

Scheme 47 Fe-catalyzed hydrosilane reduction of amides to amines...

Diborane also reduces amides to amines (see Section 5.3.1.2). 

Alane is also a useful group for reducing amides and it, too, can be used to reduce amides to amines in the presence of ester groups. 

Reduction of Amides to Amines Dihydro-deoxo-bisubstitution... 

Access to this type of compound is illustrated in Scheme 30 by the preparation of retro-sulfonamide tripeptide Boc-Pro-Leuijt[NH—S02]Gly-NH2(78). The two false termini used are the prochiral gem-diamino analogue of Leu and sulfoacetic acid. Amide to amine conversion according to Hofmann, carried out on the dipeptide Boc-Pro-Leu-NH2 (76) with iodobenzene l,l-bis(trifluoroacetate) gave the gem-diamino derivative 77. Coupling of the resulting gem-diamino derivative with methyl (chlorosulfonyl)acetate, followed by amida-tion of the intermediate methyl ester, afforded the desired pseudopeptide 78J1341 Full experimental details have not yet been reported. 

Review. Moriarty and Koser3 have reviewed this hypervalent iodine(III) compound. It is particularly useful for vie, ciy-ditosyloxylation of alkenes, a-tosylation of ketones, and conversion of primary amides to amines. 

Rearrangement of primary amides to amines induced by BTI RCONH2 -4 RNH2... 

Reductions.1 The reactivity of LiBH4 (or NaBH4) in THF is markedly enhanced by ClSi(CH3)3. The resulting reagent reduces amino acids to optically pure amino alcohols, and amides to amines. The active agent is believed to be a complex of BH3 and THF. The combination of these two reagents also forms LiCl and (CH3)3SiH. 

O II RCNHR 1) LiAlH4 2) H20 RCH2NHR Section 19.7 Reduction of amides to amines. 

The ruthenium cluster Ru3(CO)12 and the RuCl2(CO)2(PPh3)2 system with ethyl or methyl iodide and additionally with diethyl amine as cocatalyst(s) have shown high catalytic activity in facile transformation of cyclic and acyclic amides to amines via hydrosilylation with many trisubstituted silanes (Eq. 94) [149],... 

What are the alternatives There are two main ones, and both involve functional group interconversion, with the reactive amine being converted to a less reactive derivative before disconnection. The first solution is to convert the amine to an amide and then disconnect that. The reduction of amide to amine is quite reliable, so the FGI is a reasonable one. 

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