November 17, 2019, 01:13:02 AM
Forum Rules: Read This Before Posting


Topic: long total synthesis problem  (Read 8842 times)

0 Members and 1 Guest are viewing this topic.

haiph12

  • Guest
long total synthesis problem
« on: March 15, 2004, 10:42:33 AM »
help me to cpmplete this scheme


Edit: edited title for better indexing. Mitch
« Last Edit: April 24, 2004, 07:11:40 PM by Mitch »

haiph12

  • Guest
Re:help me (continuous)
« Reply #1 on: March 17, 2004, 09:56:24 AM »
why nobody help me?

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 6857
  • Mole Snacks: +489/-81
  • Gender: Male
Re:help me (continuous)
« Reply #2 on: March 17, 2004, 12:19:46 PM »
Just start from formulas of both parent substances: C6H5NO and C5H9NO. As you can see the product A shows sum of atoms from both formula. So addition facilitated by ethoxide anion take place at alpha carbon of pyrolidone
and alcohol group is formed from aldehyde group. Then this OH group is oxidised to carbonyl one (product B)
B can enolise (two beta-carbonyl groups) and can attach one HCl to double bond and hydrolyse to carboxylic acid - amino group joins the next HCl (product C -add H2O over arrow between B and C). Next step is decarboxylation of acid (product D) followed by neutralisation and elimination of HCl
(product E - C6H4N-CO-CH2-CH2-CH2-NH-CH3). Then reduction of CO to CHOH (product F) followed
by exchang  of OH by I (product G) and elimination of HI produce C5H4N-CH=CH CH2-CH2-NH-CH3 product N). I doubt if the final product could exist in open ring form - it rather cyclises to N-methyl pyrolidine.
AWK
« Last Edit: March 17, 2004, 12:55:34 PM by AWK »
AWK

haiph12

  • Guest
Re:help me (continuous)
« Reply #3 on: March 18, 2004, 09:06:30 AM »
the first  thank you AWK for every thing.
You study organic chemistry very much,don't you.
second , final product( N ) ( cyclises to N-methyl pyrolidine is true) because N  is Nicotin  and is optical active compound.
Can you help me  complete the scheme( in topic : do you solve the problem) ?
Thank you very much AWK

Offline AWK

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 6857
  • Mole Snacks: +489/-81
  • Gender: Male
Re:help me (continuous)
« Reply #4 on: March 19, 2004, 03:34:22 AM »
Though nicotine is an optical active compunds, your total synthesis gives a mixture of enantiomers
AWK

haiph12

  • Guest
Re:help me (continuous)
« Reply #5 on: March 19, 2004, 03:55:06 AM »
Yes,
and the scheme in topic : do you solve the problem
can you help me?
help me
Thank.

Sponsored Links