CAS: 174060-98-1; (S)-1-(Tert-Butoxycarbonyl)-3,3-Dimethylpyrrolidine-2-Carboxylic Acid

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1982344-79-5 61406-78-8 76804-64-3

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tert-butyl dicarbonatedi-tert-butyl dicarbonate (2S)-3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester (2S)-3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (2S,4R)-3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl ester

📜(2S,4S)-3,3-Dimethyl-4-Hydroxy-N-(9-Phenylfluoren-9-yl)Proline Benzyl Ester置于palladium Dihydroxide 偶氮二异丁腈,氢气,三正丁基氢锡,Sodium Hydride体系中,用 四氢呋喃,甲苯 用作溶剂,4.0 °C,506.62 Kpa 条件下,反应 26.5H,反应生成(S)-N-Boc-3,3-二甲基吡咯烷-2-甲酸
参考文献:Regioselective Enolization And Alkylation Of 4-Oxo-N-(9-Phenylfluoren-9-yl)Proline: Synthesis Of Enantiopure Proline−valine And Hydroxyproline−valine Chimeras
标题:Regioselective Enolization And Alkylation Of 4-Oxo-N-(9-Phenylfluoren-9-yl)Proline: Synthesis Of Enantiopure Proline−valine And Hydroxyproline−valine Chimeras
摘要:The Regioselective Enolization Of 4-Oxo-N-(9-Phenylfluoren-9-yl)Proline Benzyl Ester (5) Followed By Alkylation With Different Alkyl Halides Has Been Used To Synthesize A Variety Of Beta-Alkylproline Derivatives. In Particular,Enolization Of 5 With 400 Mol % Of Kn(Sime(3))(2) And Alkylation With Iodomethane Provided 3,3-Dimethyl-4-Oxo-N-(9-Phenylfluoren-9-yl)Proline Benzyl Ester (7A) In Excellent Yield. Subsequent Hydride Reduction Of Ketone 7A And Protecting Group Exchange By Hydrogenation In The Presence Of Di-Tert-Butyl Dicarbonate Provided Enantiopure (2S,4R)-And (2S,4S)-3,3-Dimethyl-4-Hydroxy-N-(Boc)Prolines. 2. Hydroxyproline-Valine Chimeras (2S,4R)-And (2S,4S)-2 Are Each Synthesized From Hydroxyproline In Six Steps And 27% Respective Overall Yield. Deoxygenation Of 3,3-Dimethyl-4-Hydroxy-N-(9-Phenylfluoren-9-yl)Proline Benzyl Esters 9 Via Their Conversion To Xanthates 10 Followed By Tributylstannane-Mediated Reduction Provided 3,3-Dimethyl-N-(9-Phenylfluoren-9-yl)Proline Benzyl Ester (11) In Excellent Yield. Hydrogenation Of 11 With Pearlman'S Catalyst In The Presence Of Di-Tert-Butyl Dicarbonate Then Furnished (2S)-3,3-Dimethyl-N-(Boc)Proline (1) In The Last Step Of An Eight-Step Synthesis (41% Overall Yield) From Hydroxyproline. Both Proline-Valine And Hydroxyproline-Valine Chimeras 1 And 2 Were Designed To Serve As Tools For Studying The Conformational Requirements Of Biologically Active Peptides.
Doi:10.1021/jo9514984