Complete reaction mechanism (arrow pushing mechanism, resonance stabilization, charges) Question 8In the first asymmetric synthesis of (-)-(S,S)-homaline, a symmetric alkaloid isolated in the early 1970s, a keyintermediate was compound 2 (Tetradhedron Lett. 2012, 53, 1119-1121). Provide the reagents for convertingcompound 1 into compound 2. Make the tertiary amine at first.MeHNTwo stepscO,MecO,MePh1Choose from the list of reagents:NH2NH2H3O*, NABH3CNH3O*, NABH3CNH3O°, NABH3CNb.C.a.d.H3CH3O*, NABH;CNH3O*, NABH3CNCH3H3O“, NaBH3CNH.f.е.HCHHg. NazCr207, H,SO4, H2Oh. xs Crog, H3O", acetonei. PCC, CH2CI2j. NABH4, MEOHk. 1) xs LAH 2) H20I. NaN3Step 1Step 222.90. Two steps are required. The secondary amine must be methylated to give atertiary amine, and the halogen (CI) must be replaced with azide. The first step can beachieved via a reductive amination (the nitrogen atom cannot simply be methylated byusing Mel, because that would result in over-alkylation, giving the quaternary salt, RạN*N. Then, in the second step, Cl can function as a leaving group in an Sy2 reaction withsodium azide, to afford compound 2.Me.Me.HN[H1 NABH,CN.co,Me.cO.MecOMePhPhPh

Converting compound 1 to 2. The functional group changes are: Change of secondary amine to tertiary…

Question 8 In the first asymmetric synthesis of (-)-(S,S)-homaline, a symmetric alkaloid isolated in the early 1970s, a key intermediate was compound 2 (Tetradhedron Lett. 2012, 53, 1119-1121). Provide the reagents for converting compound 1 into compound 2. Make the tertiary amine at first. `Ng Me. HN Two steps CO_Me .CO.Me Ph Ph Choose from the list of reagents: NH2 NH2 a. H3O°, NABH3CN b. H3O*, NABH3CN H3O", NABH3CN d. H3C H3O°, NABH;CN CH3 H30*, NABH,CN CH, f. H3O*, NABH3CN е. g. NazCr,07, H2SO4, H20 h. xs Crog, H3O", acetone i. PCC, CH2CI2 j. NABH4, MEOH k. 1) xs LAH 2) H20 I. NaN3 Step 1 f Step 2 I 22.90. Two steps are required. The secondary amine must be methylated to give a tertiary amine, and the halogen (CI) must be replaced with azide. The first step can be achieved via a reductive amination (the nitrogen atom cannot simply be methylated by using Mel, because that would result in over-alkylation, giving the quaternary salt, RaN* N. Then, in the second step, Cl can function as a leaving group in an Sy2 reaction with sodium azide, to afford compound 2. Me NaNg Me HN [H1 NABH,CN Co,Me .cOMe Ph Ph Ph 2

Question 8 In the first asymmetric synthesis of (-)-(S,S)-homaline, a symmetric alkaloid isolated in the early 1970s, a key intermediate was compound 2 (Tetradhedron Lett. 2012, 53, 1119-1121). Provide the reagents for converting compound 1 into compound 2. Make the tertiary amine at first. `Ng Me. HN Two steps CO_Me .CO.Me Ph Ph Choose from the list of reagents: NH2 NH2 a. H3O°, NABH3CN b. H3O, NABH3CN H3O", NABH3CN d. H3C H3O°, NABH;CN CH3 H30, NABH,CN CH, f. H3O, NABH3CN е. g. NazCr,07, H2SO4, H20 h. xs Crog, H3O", acetone i. PCC, CH2CI2 j. NABH4, MEOH k. 1) xs LAH 2) H20 I. NaN3 Step 1 f Step 2 I 22.90. Two steps are required. The secondary amine must be methylated to give a tertiary amine, and the halogen (CI) must be replaced with azide. The first step can be achieved via a reductive amination (the nitrogen atom cannot simply be methylated by using Mel, because that would result in over-alkylation, giving the quaternary salt, RaN N. Then, in the second step, Cl can function as a leaving group in an Sy2 reaction with sodium azide, to afford compound 2. Me NaNg Me HN [H1 NABH,CN Co,Me .cOMe Ph Ph Ph 2

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.39P

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