Ethanol → (R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 924424Notes

Reaction equation

HRID 924424 reaction equation
[Li+].[BH4-].C([C@@H]1COC(=O)N1[C:16](=[O:42])[C@H:17]([CH3:41])[C@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])C1C=CC=CC=1.CCO>C1COCC1.CCOCC.[OH-].[Na+]>[Si:20]([O:19][C@@H:18]([C@H:27]1[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[N:28]1[C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@@H:17]([CH3:41])[CH2:16][OH:42])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 68547408(R)-tert-butyl 4-((1R,2R)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(tert-butyldimethylsilyloxy)-2-methyl-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59226545(R)-tert-butyl 4-((1R,2S)-1-(tert-butyldimethylsilyloxy)-3-hydroxy-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylateYield 78.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

LiBH4 (0.25 g, 11 mmol) was added to a mixture of tert-butyl (4R)-4-((1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-1-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxopropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (2.2 g, 3.8 mmol) and EtOH (0.67 mL, 11 mmol) in THF (40 mL) at −30° C. The mixture was allowed to warm to 0° C. and stirred for 3 h. The reaction mixture was then diluted with Et2O and 1 M NaOH was added. The resulting mixture was extracted with EtOAc. The separated organic extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluting with 0-20% EtOAc in hexanes) to give the sub-title compound (1.2 g, 78%). LCMS calc. for C15H34NO3Si (M+H-Boc)+: m/z=304.2. found 304.2.

Workup

  1. additionwas added
  2. extractionThe resulting mixture was extracted with EtOAc
  3. extractionThe separated organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (eluting with 0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4bba70857d5843818dc445dae103b2a8
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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