Chemistry Forums for Students > Organic Chemistry Forum

Carbonyl compound synthtetic pathway

(1/2) > >>

claire88:
I was trying to figure out a way to convert this compound:

CH2=CHCHO

to this one:

CH3CH(NH2)CH2COOH


I've managed to figure out a couple of steps, like:

1) CH2=CHCHO ---> CH3CH(Br)CHO

2) CH3CH(Br)CHO ---> CH3CH(NH2)CHO

And this is where I'm stuck... How do you convert 2-aminopropanal to 3-aminobutanoic acid? I tried nucleophilic addition with KCN but that gave me a nitrile with an unwanted alcohol group.

The answer is probably quite simple but I can't for the life of me figure it out!

Thanks :)

Nucleophile:
I am not sure how far are you into your studies, but I've got a number of paths with organometallics that might be useful.

claire88:

Such as the Grignard reagent?

Nucleophile:
Grignard is a classic example of an organometallic reagent, but it will harmful to our efforts. ;D

Let me try to think of something else up in a couple of secs.

claire88:

Grignard's the only organometallic reagent that's in our syllabus, though :(

And you're right, it didn't work when I tried that out!

Navigation

[0] Message Index

[#] Next page