2,2,2-Trifluoroethanol → HCID 59347045, compound

HRID 1009128Notes

Reaction equation

HRID 1009128 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].Cl[C:10]1[CH:15]=[C:14]([CH2:16][C@H:17]2[C@@H:21]([CH2:22][OH:23])[O:20][C:19]([CH3:25])([CH3:24])[N:18]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:13]=[CH:12][N:11]=1>CN1C(=O)CCC1.CCOC(C)=O>[OH:23][CH2:22][C@H:21]1[O:20][C:19]([CH3:24])([CH3:25])[N:18]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[C@H:17]1[CH2:16][C:14]1[CH:15]=[CH:10][N:11]=[C:12]([O:8][CH2:3][C:4]([F:7])([F:6])[F:5])[CH:13]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 59347033(4S,5S)-Tert-butyl 4-((2-chloropyridin-4-yl)methyl)-5-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59347045HCID 59347045, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% by weight in mineral oil) (0.672 g, 16.8 mmol) was added carefully to trifluoroethanol (20.0 ml, 276 mmol) cooled at 0° C. and then stirred at RT for 30 minutes. The resulting solution is added to (4S,5S)-tert-butyl 4-((2-chloropyridin-4-yl)methyl)-5-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate (0.400 g, 1.12 mmol) dissolved in 10 mL of NMP and the resulting solution was microwaved for 30 minutes fixed at 180° C. The reaction was diluted with EtOAc and washed repeatedly with water. The combined aqueous layers were back extracted with EtOAc and the combined organic layers were washed with water, brine, dried over sodium sulfate and concentrated. The product was purified by silica gel chromatography (2:1 to 1:1 Hexanes/EtOAc) to afford the title compound. MS m/z: 421.3 (100%, M+1).

Workup

  1. customthe resulting solution was microwaved for 30 minutes
  2. customfixed at 180° C
  3. washwashed repeatedly with water
  4. extractionThe combined aqueous layers were back extracted with EtOAc
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by silica gel chromatography (2:1 to 1:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-67375c344dca46b6b0a8fb751d42ca99
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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