Piperazinone derivatives, such as compound 4, are being investigated for their potential use in the treatment of migraines as well as a variety of other diseases, including hypertension and sepsis. The following two-step synthetic procedure was developed as a general method for producing a variety of piperazinone derivatives (Tetrahedron Lett. 2009, 50, 3817-3819). Compound 1 is a readily available starting material that can be converted to compound 2 via an SN2 process. Reductive amination of compound 2 affords compound 3 which is short-lived and rapidly undergoes acid-catalyzed amide formation to the cyclic product 4a, piperazinone derivative. 1 H₂N. Br OMe NaHCO3 DMF Challenge Problem 22.100a Incorrect. OMe 2 PhCH,NH NaBH3CN 3 AcOH, heat Draw the structure of compound 3. If it is a pair of diastereomers, draw both diastereomers. Do NOT use abbreviations such as Ph or OMe when drawing the structure(s). Draw Your Solution

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Piperazinone derivatives, such as compound 4, are being investigated for their potential use in the treatment of migraines as well as a
variety of other diseases, including hypertension and sepsis. The following two-step synthetic procedure was developed as a general
method for producing a variety of piperazinone derivatives (Tetrahedron Lett. 2009, 50, 3817-3819). Compound 1 is a readily available
starting material that can be converted to compound 2 via an SN2 process. Reductive amination of compound 2 affords compound 3
which is short-lived and rapidly undergoes acid-catalyzed amide formation to the cyclic product 4a, piperazinone derivative.
1
H₂N.
OMe
Br
NaHCO3
DMF
2
PhCH, NH
NaBH3CN
AcOH, heat
4
[3]
Challenge Problem 22.100a
Incorrect.
OMe
Draw the structure of compound 3. If it is a pair of diastereomers, draw both diastereomers. Do NOT use abbreviations such as Ph
or OMe when drawing the structure(s).
Draw Your Solution
Transcribed Image Text:Piperazinone derivatives, such as compound 4, are being investigated for their potential use in the treatment of migraines as well as a variety of other diseases, including hypertension and sepsis. The following two-step synthetic procedure was developed as a general method for producing a variety of piperazinone derivatives (Tetrahedron Lett. 2009, 50, 3817-3819). Compound 1 is a readily available starting material that can be converted to compound 2 via an SN2 process. Reductive amination of compound 2 affords compound 3 which is short-lived and rapidly undergoes acid-catalyzed amide formation to the cyclic product 4a, piperazinone derivative. 1 H₂N. OMe Br NaHCO3 DMF 2 PhCH, NH NaBH3CN AcOH, heat 4 [3] Challenge Problem 22.100a Incorrect. OMe Draw the structure of compound 3. If it is a pair of diastereomers, draw both diastereomers. Do NOT use abbreviations such as Ph or OMe when drawing the structure(s). Draw Your Solution
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