Trimethylsilyldiazomethane → 1-tert-butyl 2-methyl (2S,4R)-4-[(7-bromo-6-methoxyisoquinolin-1-yl)oxy]pyrrolidine-1,2-dicarboxylate
反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:15]([C:25]([OH:27])=[O:26])[CH2:14]2)=[CH:4][C:3]=1[O:28][CH3:29].[Si](C=[N+]=[N-])(C)(C)[CH3:31]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[O:12][C@H:13]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[C@H:15]([C:25]([O:27][CH3:31])=[O:26])[CH2:14]2)=[CH:4][C:3]=1[O:28][CH3:29]参加物
実験手順
To a solution of compound 122 in MeOH (0.1 M) was added TMS-diazomethane (4.2 eq.) and the mixture was stirred at RT for 20 min. Volatiles were evaporated and the crude purified by chromatography to obtain 1-tert-butyl 2-methyl (2S,4R)-4-[(7-bromo-6-methoxyisoquinolin-1-yl)oxy]pyrrolidine-1,2-dicarboxylate as a pale orange foam (79%). To the previous compound dissolved in toluene (0.1 M) tetrakis-(triphenylphospin)-palladium(0) (0.1 eq.) and vinyltri-N-butyltin (1 eq) were added and the mixture was heated at 100° C. for 20 h. Volatiles were evaporated and the residue purified by chromatography to obtain 1-tert-butyl 2-methyl (2S,4R)-4-[(6-methoxy-7-vinylisoquinolin-1-yl)oxy]pyrrolidine-1,2-dicarboxylate as a pale yellow foam (45%) that was treated with HCl 4N in dioxane (26 eq) at RT. After 30 min volatiles were evaporated to obtain the title compound 123 in quantitative yield. MS (ES+) m/z 329 (M+H)+.
後処理
- customVolatiles were evaporated
- customthe crude purified by chromatography
出典と根拠
- ORDレコード
- ord-68ea369b0d04406da0d5d08803629714
- 出典データセット
- uspto-grants-2012_11
- 特許番号
- US08314062B2
反応ノート
読み込み中…