tert-Butyl methyl ether → (2S,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propan-1-ol

HRID 1021155ノート

反応式

HRID 1021155 の反応式
C([C@H]1COC(=O)N1[C:14](=[O:30])[C@H:15]([CH3:29])[C@@H:16]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=1)[O:17][Si:18]([CH3:21])([CH3:20])[CH3:19])C1C=CC=CC=1.[Li+].[BH4-].[NH4+].[Cl-].CC(OC)(C)C>C1COCC1>[Br:28][C:24]1[CH:23]=[C:22]([C@@H:16]([O:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[C@@H:15]([CH3:29])[CH2:14][OH:30])[CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 4

HCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 66743729(S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one

生成物 1

HCID 57956785(2S,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propan-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (S)-4-benzyl-3-((2R,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propanoyl)oxazolidin-2-one in anhydrous THF is added a solution of LiBH4 in THF under argon. The reaction mixture is stirred for 18 h at room temperature and a saturated aqueous solution of NH4Cl is slowly added followed by MTBE. The mixture is stirred for 15 mins, layers are separated, organic layer is washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (5 to 40% EtOAc/hexane gradient) to give (2S,3S)-3-(3-bromophenyl)-2-methyl-3-(trimethylsilyloxy)propan-1-ol.

後処理

  1. stirringThe mixture is stirred for 15 mins
  2. customlayers are separated
  3. washorganic layer is washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography (5 to 40% EtOAc/hexane gradient)

出典と根拠

ORDレコード
ord-d0fbbfea3a744c22b4a0e6bfb3588a09
出典データセット
uspto-grants-2014_05
特許番号
US08716529B2

反応ノート

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