3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)- → HCID 68839236、化合物

HRID 660559

反応式

HRID 660559 の反応式
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:43]([O:47][C:48]([N:50]1[C@H:54]([CH:55]=O)[CH2:53][O:52][C:51]1([CH3:58])[CH3:57])=[O:49])([CH3:46])([CH3:45])[CH3:44]>C1(C)C=CC=CC=1>[C:43]([O:47][C:48]([N:50]1[C@H:54]([CH:55]=[CH:9][C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:53][O:52][C:51]1([CH3:57])[CH3:58])=[O:49])([CH3:46])([CH3:44])[CH3:45]

参加物

5

反応物 3

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 3251421Potassium bis(trimethylsilyl)amideHCID 19092713{[2-(Ethoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

生成物 1

HCID 68839236HCID 68839236、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a suspension of (2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide (9.0 g, 17.77 mmol) in toluene (100 mL) is added potassium bis(trimethylsilyl)amide (0.5M in toluene, 40 mL) followed by the addition of (S)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (3.4 g, 14.83 mmol) and the mixture is refluxed for 1 h. After cooling to RT, ice/water is added and the solution extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography to afford the title compound as a yellow oil: (M+1)+=376.

後処理

  1. temperaturethe mixture is refluxed for 1 h
  2. extractionthe solution extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material is purified by column chromatography

出典と根拠

ORDレコード
ord-4796e25e8e5a4414b94bcacc3d4b7926
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

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