Synthesis help: cyclohexylmethanamine from cyclohexanone

[combatwombat]

I have a way of doing this but I feel like there's got to be a quicker route. Here's how I did it:

 

1. HCN

2. LiAlH4

3. H2O

4. H2SO4, -H2O

5. H2, Pd

 

(i.e. cyanohydrin formation, reduction, acid-catalyzed elimination to get rid of OH, then H2/Pd to get rid of double bond)

 

Could it maybe be done with a Wittig reagent?

[UC]

I have a way of doing this but I feel like there's got to be a quicker route. Here's how I did it:

 

1. HCN

2. LiAlH4

3. H2O

4. H2SO4, -H2O

5. H2, Pd

 

(i.e. cyanohydrin formation, reduction, acid-catalyzed elimination to get rid of OH, then H2/Pd to get rid of double bond)

 

Could it maybe be done with a Wittig reagent?

 

You have two reductions. I'm not sure, but you may be able to do both with the hydrogen and Pd on carbon.

 

Alternative to cyanohydrin: http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0221