Water → tert-Butyl(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxo-pyrrolidine-1-carboxylate

HRID 1173586ノート

反応式

HRID 1173586 の反応式
[OH:1][C@@:2]1([CH3:15])[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:3]1[CH3:14].O.I([O-])(=O)(=O)=[O:18].[Na+]>C(OCC)(=O)C.O.[Ru](=O)=O>[OH:1][C@@:2]1([CH3:15])[CH2:6][C:5](=[O:18])[N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:3]1[CH3:14]

参加物

6

反応物 3

HCID 962WaterHCID 11622622tert-butyl (2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylateHCID 23667635Sodium periodate

生成物 1

HCID 59556959tert-Butyl(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxo-pyrrolidine-1-carboxylate収率 34.2%

試薬・触媒・溶媒 2

HCID 16211523Ruthenium dioxide hydrate触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of tert-butyl(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidine-1-carboxylate (3.05 g) in ethyl acetate (45 mL) were successively added water (68 mL), ruthenium dioxide monohydrate (566 mg) and sodium periodate (4.57 g) at room temperature. The mixture was stirred at room temperature for 40 hr, the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate. The obtained organic layers were mixed, isopropanol (0.7 mL) was added, and the mixture was stirred at room temperature for 5 min. The reaction solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10→4/10) to give the title compound as a white powder (yield: 1.11 g, 34%).

後処理

  1. customat room temperature
  2. customthe organic layer and the aqueous layer were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. additionThe obtained organic layers were mixed
  5. additionisopropanol (0.7 mL) was added
  6. stirringthe mixture was stirred at room temperature for 5 min
  7. dry with materialThe reaction solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10→4/10)

出典と根拠

ORDレコード
ord-8c3ee090fe904fc2a84ecd8c3a41c5f5
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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