Benzyl chloroformate → (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate

HRID 340929ノート

反応式

HRID 340929 の反応式
[Si:1]([O:8][CH2:9][C@H:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].[CH:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][C:30](Cl)=[O:31])=[CH:24][CH:23]=1>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:11][CH2:12][C:13](=[O:15])[N:14]1[C:30]([O:29][CH2:28][C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1)=[O:31])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 10263224(S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-2-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 12078685(S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate収率 91.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one (48.5 g, 0.21 mol) in THF (100 mL) was added t-BuOK (30.8 g, 0.27 mol) at 0° C. The mixture was stirred at 0° C. for 30 min followed by addition of Cbz-Cl (40.4 mL, 0.27 mol) dropwise at 0° C. The resulting mixture was stirred at RT overnight, quenched with saturated NH4Cl, concentrated to a small amount, and diluted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-benzyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate (70 g, 91%). LRMS (M+H−44) m/z 320.2.

後処理

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customquenched with saturated NH4Cl
  3. concentrationconcentrated to a small amount
  4. additiondiluted with EtOAc
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified on silica gel column
  10. additiona mixture of EtOAc and hexanes

出典と根拠

ORDレコード
ord-33955cdcddea4e98bff807c889bda423
出典データセット
uspto-grants-2014_11
特許番号
US08895582B2

反応ノート

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