[maverick1996]

I'm a first year undergrad - just doing some practice with organic chem and came across this question
Didn't know how to go about doing it, can somebody help??

the question says that other readily available organic starting materials are available

Thanks in advance

[Borek]

You have to show your efforts at solving the problem to receive help, this is a forum policy.

[maverick1996]

You have to show your efforts at solving the problem to receive help, this is a forum policy.

thank you for telling me this

I tried using ozone with a Zn cat. to cleave the double bond
The i though of making an oxime and reducing that with LiAlH4 to make an amine
and then react this amine with an aldehyde to make an Imine
Reducing this imine with NaBH4 maybe??

But the thing that was really confusing me is the alcohol group

I don't really know - I have never really seen a question like this

Thank you

[discodermolide]

Reduction will give the amine.
How do amines react with epoxides?

[Alwin Kristen]

sounds like a plan  From what would you do an oxime?

[maverick1996]

sounds like a plan  From what would you do an oxime?

I honestly don't know - this has been bugging me for a while

[maverick1996]

Reduction will give the amine.
How do amines react with epoxides?

Uhm I'm not quite sure, haven't come across an amine reacting with an epoxide so far in my undergrad - but I'm guessing it's going to be a standard SN2 reaction??

I'm probably wrong though

[AWK]

https://www.wikiwand.com/en/Ethylene_oxide

[maverick1996]

https://www.wikiwand.com/en/Ethylene_oxide

Cheers mate

[Alwin Kristen]

I wonder if it is even necessary to make oxime from anything. Can you react primary amine with pivaladehyde which you get from cleaving doublebond with ozone? Is there commercially available primary amine you could use?

[maverick1996]

Thanks for all your help

What do you think of this?

[AWK]

Instead HOCH2COCl(easy cyclization of 2 molecules) use ClCH2CH2OH(epichlorohydrine) or oxirane. A few steps less.

[kriggy]

You could also get aldehyde from the ozonolysis and then do reductive amination that will save you some steps