ORGLIST: Re: deprotection of amine

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From: Krupa Shukla (krupa_shukla$##$yahoo.com)
Date: Fri Oct 14 2005 - 21:53:19 EDT



hi

u can try 40% KOH/ water in about 1:1 ratio with
refluxing conditions. (note that amine solubility in
water remains quite high. so several extractiions may
be required)

krupa




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> Today's Topics:
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> 1. help regarding deprotection of Amine group
> (Mr. (Dr.) Hardik M. Thakar)
> 2. Re: Diol protection of Triol such as Glycerol
> or TMP with
> Ketone (Mr. (Dr.) Hardik M. Thakar)
> 3. RE: help regarding deprotection of Amine
> group (will jones)
>
>
>
----------------------------------------------------------------------
>
> Message: 1
> Date: 13 Oct 2005 05:52:04 -0000
> From: "Mr. (Dr.) Hardik M. Thakar"
> <hardikthakar$##$rediffmail.com>
> Subject: ORGLIST: help regarding deprotection of
> Amine group
> To: everybody$##$orglist.net
> Message-ID:
> <20051013055204.392.qmail$##$webmail53.rediffmail.com>
> Content-Type: text/plain; charset="iso-8859-1"
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> Dear All,
>
> I protected my amine group with ethyl carbamate
> (NHCOOEt) some body help me to deprotect it.
>
> Sincerely,
>
> Hardik Thakar
>
> Thakar Hardik M.
> Ph.D. Student,
> B V Patel PERD Centre,
> S G Road,
> Thaltej,
> Ahmedabad-380054,
> India.
> Mob. No. :-+91-9825877320
> Fax. +91-79-27450449
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> Message: 2
> Date: 14 Oct 2005 03:26:18 -0000
> From: "Mr. (Dr.) Hardik M. Thakar"
> <hardikthakar$##$rediffmail.com>
> Subject: Re: ORGLIST: Diol protection of Triol such
> as Glycerol or TMP
> with Ketone
> To: "William Chien" <billychien$##$yahoo.com>
> Cc: everybody$##$orglist.net
> Message-ID:
> <20051014032618.11717.qmail$##$webmail7.rediffmail.com>
> Content-Type: text/plain; charset="iso-8859-1"
>
>
> please try p-toluene sulphonic acid in amount of
> 1:0.2 mol
>
> Sincerely,
> Hardik
>
> On Thu, 13 Oct 2005 William Chien wrote :
> >Several years ago, I was trying to make a diol (of
> >Trimethylolpropane)protecting group by using
> dimethyl
> >ketone and found the resulting material wasn't very
> >stable.
> >
> >Recently I found an article regarding a similar
> >reaction (Glycerol with Ketone and acidic
> catalyst).
> >
> >I am looking for the type of catalyst suitable for
> >this reaction and the reaction condition to
> stabilise
> >the resulting compound.
> >
> >Thanks and best regards
> >
> >William
> >
> >
> >
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> Message: 3
> Date: Fri, 14 Oct 2005 08:59:49 +0000
> From: "will jones" <willjones46$##$hotmail.com>
> Subject: RE: ORGLIST: help regarding deprotection of
> Amine group
> To: hardikthakar$##$rediffmail.com,
> everybody$##$orglist.net
> Message-ID:
> <BAY102-F18FAF54C8525B9C655FA5BAE7D0$##$phx.gbl>
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>
> Have you tried TMSI/base hydrolysis?
>
> If that doesnt work with your system, pick an amine
> protecting group that
> is!!
>
> A decent quick overview found here.
>
>
http://cook.chem.ndsu.nodak.edu/files/worms/050223-worms-grc-nprot.pdf
>
> Will
>
>
> >From: "Mr. (Dr.) Hardik M. Thakar"
> <hardikthakar$##$rediffmail.com>
> >Reply-To: "Mr. (Dr.) Hardik M. Thakar"
> <hardikthakar$##$rediffmail.com>
> >To: everybody$##$orglist.net
> >Subject: ORGLIST: help regarding deprotection of
> Amine group
> >Date: 13 Oct 2005 05:52:04 -0000
> >
> >
> >Dear All,
> >
> >I protected my amine group with ethyl carbamate
> (NHCOOEt) some body help me
> >to deprotect it.
> >
> >Sincerely,
> >
> >Hardik Thakar
> >
> >Thakar Hardik M.
> >Ph.D. Student,
> >B V Patel PERD Centre,
> >S G Road,
> >Thaltej,
> >Ahmedabad-380054,
> >India.
> >Mob. No. :-+91-9825877320
> >Fax. +91-79-27450449
>
>
> >_______________________________________________
> >ORGLIST - Organic Chemistry Mailing List
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