Potassium Carbonate → HCID 59625488, compound

HRID 2192874Notes

Reaction equation

HRID 2192874 reaction equation
FC(F)(F)C([NH:5][CH:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:5][CH:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 596253502(1H)-Isoquinolinecarboxylic acid, octahydro-4-[(2,2,2-trifluoroacetyl)amino]-, 1,1-dimethylethyl ester

Product 1

HCID 59625488HCID 59625488, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-[(trifluoroacetyl)amino]octahydroisoquinoline-2(1H)-carboxylate (1.75 g) and 20% aqueous potassium carbonate solution (10 ml) in methanol (25 ml) was stirred at 60° C. for 15 hr. The solvent was evaporated under reduced pressure, saturated brine (20 ml) was added to the residue, and the mixture was extracted with chloroform (30 ml×2). The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-methanol (1:0-9:1) was concentrated under reduced pressure to give the object compound (1.12 g) as an oil.

Workup

  1. customThe solvent was evaporated under reduced pressure, saturated brine (20 ml)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with chloroform (30 ml×2)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washthe fraction eluted with ethyl acetate-methanol (1:0-9:1)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-16f57ca5028f49deb34083a67eb0b1a3
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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