Synthesis Problems 2 KEY

Synthesis Problems 2 KEY - 2 2) ! 1) MeI 2) Ag 2 O ! 1)...

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Chemistry 30C - UCLA Winter 2011 Answers to Synthesis Problems 2 Propose syntheses to accomplish the following transformations. Use any reagents necessary unless indicated. More than one route may be possible, but the number indicates one possible number of steps. 10 1 2 3 4 5 6 7 8 9 N NMe 2 Br O O O O O O O O OEt N N H NH 2 OH O Ph Ph O OH NH 2 Ph Np Np Ph Np Ph NMe 2 Ph Np 1) MCPBA CH 2 Cl 2 2) Pr-NH 2 3) Acetic anhydride Et 3 N 1) H 2 O
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Unformatted text preview: 2 2) ! 1) MeI 2) Ag 2 O ! 1) SOCl 2 2) excess NHMe 2 3) LiAlH 4 THF 1) NaCN DMF 2) LiAlH 4 THF 1) MsCl Pyr 2) NaN 3 DMF 3) LiAlH 4 THF 2) H 2 N 1) MeI 2) Ag 2 O ! 3) MeI 4) Ag 2 O ! 3) LiAlH 4 THF 1) Pyrrolidine 2a) Bromoacetone b) H 2 O HCl 1) EtONa EtOH 2) NaOH H 2 O 3) Heat H 2 N Br NMe 2 N H 1) LDA THF Me-I 5)-H 2 O 4) LDA THF Br...
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