2 3 A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blocking group to keep the nitrogen from interfering in other reactions. It plays no chemical role here. B. Along with introducing the alcohol, this reaction also sets the stereochemistry at the central carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOC group does have a physical role here in that it is very large.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question 1
Methylphenidate (trade name Ritalin) has long been used for the treatment of ADHD,
particularly in children where amphetamines (trade name: Adderall/Vyvanse) are not
recommended. Further studies showed that one of the four diastereomers of methylphenidate
was responsible for the activity. That diastereomer (compound 3 below, trade name Focalin) is
shown below. A key step in the synthesis is the introduction of the alcohol group in 2 from the
alkene in 1.
BIN
BOC
1. BH, THF
2. H₂O₂/HO-
BOC
2
N
OH
2
multiple steps
HIZ
OCH 3
Focalin (dexmethylphenidate)
A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blocking
B. Along with introducing the alcohol, this reaction also sets the stereochemistry at the central
group to keep the nitrogen from interfering in other reactions. It plays no chemical role here.
carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOC
group does have a physical role here in that it is very large.
3
Transcribed Image Text:Question 1 Methylphenidate (trade name Ritalin) has long been used for the treatment of ADHD, particularly in children where amphetamines (trade name: Adderall/Vyvanse) are not recommended. Further studies showed that one of the four diastereomers of methylphenidate was responsible for the activity. That diastereomer (compound 3 below, trade name Focalin) is shown below. A key step in the synthesis is the introduction of the alcohol group in 2 from the alkene in 1. BIN BOC 1. BH, THF 2. H₂O₂/HO- BOC 2 N OH 2 multiple steps HIZ OCH 3 Focalin (dexmethylphenidate) A. Draw a mechanism for the conversion of 1 to 2. Note the BOC group is just a large blocking B. Along with introducing the alcohol, this reaction also sets the stereochemistry at the central group to keep the nitrogen from interfering in other reactions. It plays no chemical role here. carbon. Briefly explain why this diastereomer of 2 is formed preferentially from 1. The BOC group does have a physical role here in that it is very large. 3
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