Ammonium formate → HCID 131732939, compound

HRID 2171275Notes

Reaction equation

HRID 2171275 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([NH:12][CH:13]1[CH:18]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH2:17][CH2:16][N:15](C(OCC2C=CC=CC=2)=O)[CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>[Pd].C(OCC)(=O)C.CO>[O:29]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[N:19]1[CH:18]1[CH2:17][CH2:16][NH:15][CH2:14][CH:13]1[NH:12][C:10](=[O:11])[O:9][C:5]([CH3:7])([CH3:6])[CH3:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 117643186HCID 117643186, compound

Product 1

HCID 131732939HCID 131732939, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
60 °C

Procedure

Ammonium formate (419 mg) and 10% Pd/C (84 mg) were added to an ethyl acetate/MeOH (4 ml/4 ml) solution containing benzyl 3-((tert-butoxycarbonyl)amino)-4-(1,3-dioxoisoindolin-2-yl)piperidin-1-carboxylate (419 mg) obtained in the 1st step, followed by stirring at 60° C. for 1 hour. The reaction solution was cooled to room temperature and insoluble matter was removed through Celite. Filter cake was washed with ethyl acetate and water. Subsequently, the filtrate was mixed with wash liquid and sodium chloride was added to the mixture. The organic layers were separated and washed with saturated saline. The organic layers were dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. A white solid of tert-butyl (4-(1,3-dioxoisoindolin-2-yl)piperidin-3-yl)carbamate (280 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. temperatureThe reaction solution was cooled to room temperature
  3. custominsoluble matter was removed through Celite
  4. filtrationFilter cake
  5. washwas washed with ethyl acetate and water
  6. additionSubsequently, the filtrate was mixed
  7. washwith wash liquid and sodium chloride
  8. additionwas added to the mixture
  9. customThe organic layers were separated
  10. washwashed with saturated saline
  11. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-6125cb0678e94ae7a5597073e780d8a2
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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