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

HRID 1021155Notes

Reaction equation

HRID 1021155 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d0fbbfea3a744c22b4a0e6bfb3588a09
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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