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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: YuliaSnow on January 28, 2016, 09:13:15 PM

Title: Mechanism of Reductive Amination Question
Post by: YuliaSnow on January 28, 2016, 09:13:15 PM

Can someone explain the mechanism of reductive amination of an imine to an amine using H2/Pt and NaBH4? I can't find details of how it works anywhere.

http://www.wikipremed.com/03_organicmechanisms.php?mch_code=030208_080

Also, in the last step of the rxn in the link where it goes from the imine -H2-> amine, why doesn't the N atom get a H and instead gets lone pairs? I'm confused about this because alkenes + H2 gives an alkane and both carbons have H where as in this case, the carbon gets a H but the nitrogen gets lone pairs.

Thanks

Title: Re: Mechanism of Reductive Amination Question
Post by: kriggy on January 29, 2016, 01:10:17 AM

It does get hydrogen atom, in the imine it is =NH while in the amine -NH₂. Its confusing because the lone pair is drawn in the imine but not int he final product

Title: Re: Mechanism of Reductive Amination Question
Post by: zarhym on January 31, 2016, 11:04:32 PM

http://www.organic-chemistry.org/abstracts/literature/717.shtm

If you are doing a reaction, try this first. If you are just wondering about the mechanism, read the paper.