2. The following pyrrole derivative is a drug under development for schizophrenia and it is prepared by Knorr synthesis. Identify the structure of the two starting materials (ketone and a-aminoketone) required for the synthesis. -CH3 H H3C. CH3 Also, assign the absolute stereochemistry to the chiral centres contained in this drug.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter22: Synthesis Workshop 2
Section: Chapter Questions
Problem 6CTQ
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Solve Q1. with all the sub parts and the Q2 with answer and detailed explanations

2. The following pyrrole derivative is a drug under development for schizophrenia and it is
prepared by Knorr synthesis. Identify the structure of the two starting materials (ketone
and a-aminoketone) required for the synthesis.
CH3
H.
H3C.
-CH3
H
H
Also, assign the absolute stereochemistry to the chiral centres contained in this drug.
Transcribed Image Text:2. The following pyrrole derivative is a drug under development for schizophrenia and it is prepared by Knorr synthesis. Identify the structure of the two starting materials (ketone and a-aminoketone) required for the synthesis. CH3 H. H3C. -CH3 H H Also, assign the absolute stereochemistry to the chiral centres contained in this drug.
1. Using curved arrows, draw the mechanism of the following reactions:
a)
R1
catalytic H*
H2N-R
R
R
R
R
- H20
b)
H.
Keto-Enol
R
OEt
R
OEt
нн
Equilibrium
H.
c)
Н.
'N.
H.
Imine-Enamine
R
OEt
R
OEt
нн
Equilibrium
d)
PĄS10
R
R
HCI
e)
H3PO4
R
-R
R
R
f)
R1
R2
R1
R3
H*
- 2 H20
R
N.
H.
R3
R
H2N´
`R?
Transcribed Image Text:1. Using curved arrows, draw the mechanism of the following reactions: a) R1 catalytic H* H2N-R R R R R - H20 b) H. Keto-Enol R OEt R OEt нн Equilibrium H. c) Н. 'N. H. Imine-Enamine R OEt R OEt нн Equilibrium d) PĄS10 R R HCI e) H3PO4 R -R R R f) R1 R2 R1 R3 H* - 2 H20 R N. H. R3 R H2N´ `R?
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