Methyl morpholine oxide → (2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

HRID 132685ノート

反応式

HRID 132685 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>CC#N.C(Cl)Cl.CCCCCC.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH:21]=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 2

HCID 82029Methyl morpholine oxideHCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

生成物 1

HCID 16731848(2S,3S)-tert-Butyl 3-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate収率 89.5%

試薬・触媒・溶媒 4

HCID 178419074HCID 178419074、化合物触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a solution of compound 1I (3.3 g, 9.97 mmol) in 10% CH3CN in CH2Cl2 (50 mL) at rt was added NMO (3.0 g, 25.6 mmol) followed by tetrapropyl ammonium perruthenate (300 mg, 0.85 mmol). After a mild exotherm, the reaction was stirred at rt for 4 h. The reaction was diluted with hexane (50 mL), mixed well and filtered through a plug of silica gel (˜50 g). The silica plug was washed liberally with 30% EtOAc in hexane (500 mL). Solvents were removed under vacuum. Purification by flash chromatography (silica gel, 0-15% EtOAc in hexanes) provided the title compound (2.94 g).

後処理

  1. additionmixed well
  2. filtrationfiltered through a plug of silica gel (˜50 g)
  3. washThe silica plug was washed liberally with 30% EtOAc in hexane (500 mL)
  4. customSolvents were removed under vacuum
  5. customPurification by flash chromatography (silica gel, 0-15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-2c3c61fa74214788a0fbaff4b7870649
出典データセット
uspto-grants-2008_06
特許番号
US07388027B2

反応ノート

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