HCID 178522112, compound → HCID 178522109, compound

HRID 1846802Notes

Reaction equation

HRID 1846802 reaction equation
C([O:8][C@H:9]1[CH2:12][C@H:11]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH2:10]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]1[CH2:12][C@H:11]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH2:10]1

Participants

4

Reactant 1

HCID 178522112HCID 178522112, compound

Product 1

HCID 178522109HCID 178522109, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

trans-3-(benzyloxy)-N-(pyridin-2-yl)cyclobutanecarboxamide (0.394 g, 1.40 mmol) and palladium hydroxide (0.098 g, 0.14 mmol, 20 weight % on carbon) were mixed in ethanol (5 mL). The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at 70° C. for 20 h. The reaction mixture was cooled to RT and filtered. The filtrate was concentrated, and the resulting crude product was purified via silica gel chromatography to give trans-3-hydroxy-N-(pyridin-2-yl)cyclobutanecarboxamide as an off white solid.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe resulting crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-fad087c2c0884ee58f95d65885fa6bd6
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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