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Can someone help me solve #10 a-e

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10. The synthesis of an antidepressant drug relies on many of the concepts we have learned in
class with regard to regio- and chemo-selectivity. Fill in the boxes with the products requested.
a) Fill in the two isomers of products of epoxide opening resulting from the reaction of 1 with 2.
A
B
Eto
OH
OR NaOH
OR
2
b) Circle A or B above to indicate
which one is the MAJOR product.
Explain why in ONE SENTENCE
OR LESS in the space to the right.
c) One of the isomers formed in the step above was treated with
TsCI to produce two possible isomers. Fill these in to C and D
according to which epoxides would be formed after they were
E
treated with base. Fill in the expected products for E and F.
Eto
Eto
Ph
NH3
Eto
H'
Ph
HO
OH
H
NaOH
NaOH
R
CI
Et3N
C
D
F
TsCI
Et3N
OR

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formed.
d) One route to ruboxetine used the reaction below. Provide a curved arrow mechanism that
clearly shows the role of toluenesulfonic acid (TSOH) and indicates any by-products that are
Ho
CO2 CH3 +
OH
TSOH
CO2CH3
e) The synthesis described in A-C is executed with racemic materials. In order to complete the
synthesis of a single enantiomer, compound E was treated with a chiral acid chloride. Draw the
two isomers of product that result and circle the term that best describes them.
circle one
CI
CH3
diastereomers
E
OCH3
enantiomers
Et3N
regio-isomers
11. The synthesis of the drug mirabegron requires the execution of a late-stage amide
formation reaction that relies on the regioselective reactions of two intermediates in a one-pot
sequence.
a)
Fill in the expected major and minor products of this reaction.
A (minor)
B (major)
Et &N
CH3
1 equiv.
OH
CI
CH3
OH
CH3
1 equiv.
NO 2
EtgN (1 equi

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