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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Joshua Law on August 20, 2019, 08:23:46 AM

Title: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: Joshua Law on August 20, 2019, 08:23:46 AM

Hello there!

Can anyone please tell me how to theoretically synthetize 1-cyclopentylpropan-1-amine from cyclopentene in exactly 6 steps (no more, no less steps)?

Thank you for all your answers!

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: rolnor on August 20, 2019, 09:44:32 AM

Do you have any suggestion? Is it possible to add something to the double-bond as a starting-point?

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: Babcock_Hall on August 20, 2019, 02:39:27 PM

I find that it is generally easier to work backwards from the product than the other way around.  Please show us what you have tried so far.

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: Joshua Law on August 21, 2019, 03:52:54 AM

I started with Friedel-Crafts reaction using propanoyl chloride and AlCl3, with cyclopentylpropane-1-one as a product of the first step. Then I thought about reduction of the ketone using NaBH4 and MeOH resulting into 1-cyclopentylpropane-1-ol (that's the second step). As the third step using TsCl and pyridine to create (1-chloropropyl)cyclopentane.

The problem is that everything that comes to my mind uses only 5 steps, not 6 I need.   :-\

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: rolnor on August 21, 2019, 08:14:14 AM

I draw the cuprate wrong, sorry!

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: Joshua Law on August 21, 2019, 12:41:17 PM

That's perfect, thank you!  ;)
To be honest, this way of solution really didn't come to my mind at all  ;D

Title: Re: Synthesis of 1-cyclopentylpropan-1-amine from cyclopentene
Post by: sharbeldam on August 21, 2019, 05:34:57 PM

The reason I love this site so much is that intelligent chemists who know the answers already makes the OP think before just answering it (Which is also a part of the site rules), this site has very smart chemists that we are fortunate to have to help us and pass the wisdom