The Vespiary

The Hive => Serious Chemistry => Topic started by: Protium on September 04, 2001, 07:22:00 PM

Title: Tri-alkyl silane / TFA reduction of aryl ketone
Post by: Protium on September 04, 2001, 07:22:00 PM

Well, this is my first post - and I'm here to ask if anyone has attempted the direct reduction of the benzyl -OH of pseudoephedrine to afford methamphetamine using Et3SiH / TFA ?

It's a rxn used to reduce aryl carbonyl groups back to the methylene, however, as it goes through the alcohol intermediate, you'd think this would work?  If no one writes back I'll try it out and post my write up.  Should go 99% or so according to the paper.  Not so bad, using 2.2 equiv. Et3SiH + 10-15 equiv TFA - stir.. rxn over in 15 mins..

off to the pharmacy.. 8)

Title: Re: Tri-alkyl silane / TFA reduction of aryl ketone
Post by: Rhodium on September 04, 2001, 07:42:00 PM

I believe Dave Nichols used that method to reduce a cathinone to an amphetamine in the synthesis of the compound mentioned in the thread "New amphetamine more potent than LSD" in this forum...

Title: Re: Tri-alkyl silane / TFA reduction of aryl keton
Post by: Lilienthal on September 05, 2001, 12:25:00 AM

NaBH₄ / TFA should work also.

Title: Re: Tri-alkyl silane / TFA reduction of aryl keton
Post by: jim on September 05, 2001, 03:24:00 AM

LiAlH4/ AlCl3 in ether works to reduce benzyl alcohols. REFERENCE:"The Journal of Organic Chemistry", Vol 29, yr 1964, page 110-115

Title: Re: Tri-alkyl silane / TFA reduction of aryl ketone
Post by: akata on September 05, 2001, 03:02:00 PM

Post 183270 (missing)

(The_Animal: "Triethylsilane", Stimulants) might be useful

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