Water → tert-butyl (2S,3S)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

HRID 2109746Notes

Reaction equation

HRID 2109746 reaction equation
[O:1]=[C:2](N1[C@H](C2C=CC=CC=2)COC1=O)[C@@H:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:5].C(OCC)C.O.[BH4-].[Li+]>>[OH:1][CH2:2][C@@H:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][CH:11]=1)[CH3:5]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 57634030tert-Butyl (2S,3S)-1-oxo-1-((R)-2-oxo-4-phenyloxazolidin-3-yl)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

Product 1

HCID 57634081tert-butyl (2S,3S)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamateYield 66.5%

Procedure

To a 250 mL round-bottomed flask was added tert-butyl (2S,3S)-1-oxo-1-((R)-2-oxo-4-phenyloxazolidin-3-yl)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (4.80 g, 9.7 mmol), diethyl ether (50.00 mL, 481 mmol), and water (0.19 mL, 11 mmol). The resulting solution was cooled in an ice bath. Lithium borohydride (0.23 g, 11 mmol) was added in one portion and gas evolution was observed. The ice bath was removed, and the solution was stirred for about 12 hours. The reaction was followed by LCMS and once completed, was quenched by the addition of brine. The aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 20% to 60% EtOAc in hexane, to provide tert-butyl (2S,3S)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (2.15 g, 66% yield).

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. customThe ice bath was removed
  3. customwas quenched by the addition of brine
  4. extractionThe aqueous layer was extracted with EtOAc (×3)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customchromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
  9. washeluting with a gradient of 20% to 60% EtOAc in hexane

Sources & evidence

ORD record
ord-2923e7b6106f47f2bb323595c5064528
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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