Ammonium formate → HCID 68714853, compound

HRID 1911544Notes

Reaction equation

HRID 1911544 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=2)[CH2:11][O:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[N:16]=2)[CH2:11][O:10][C:9]1([CH3:26])[CH3:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68714988HCID 68714988, compound

Product 1

HCID 68714853HCID 68714853, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2,2-dimethyl-4-(6-trifluoromethyl-pyridin-2-ylethynyl)-oxazolidine-3-carboxylic acid tert-butyl ester (0.58 g, 1.56 mmol) in methanol (8 ml) were added ammonium formate (0.983 g, 15.6 mmol) and palladium on charcoal (10% Pd, 0.58 g). The mixture was refluxed for 1 hour. After cooling the solid was filtered off, the filtrate was evaporated and the residue was purified by column chromatography (SiO2, heptane/EtOAc=7:3 to yield a light colourless liquid, (0.538 g, 92%); MS (ISP): 375.5 ((M+H)+/).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperatureAfter cooling the solid
  3. filtrationwas filtered off
  4. customthe filtrate was evaporated
  5. customthe residue was purified by column chromatography (SiO2, heptane/EtOAc=7:3
  6. customto yield a light colourless liquid, (0.538 g, 92%)

Sources & evidence

ORD record
ord-25209e27413143ee92c3ff6a33f5086c
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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