8-(benzyloxy)-N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide → N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64402Notes

Reaction equation

HRID 64402 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:20])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[Si:25]([O:24][CH2:23][C@H:22]([NH:21][C:19]([C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]2=[N:17][C:16]=1[CH3:18])=[O:20])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 867134108-(benzyloxy)-N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 86713409N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamideYield 81.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5.2 g of 8-(benzyloxy)-N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 70 ml of ethanol was added 1.0 g of 10% palladium-carbon (wet), followed by stirring for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered over Celite, the solvent was then evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. To the obtained purified product were added hexane and diisopropyl ether, followed by stirring, and the resulting solid was collected by filtration and dried to obtain 3.5 g of N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography
  4. customTo the obtained purified product
  5. additionwere added hexane and diisopropyl ether
  6. stirringby stirring
  7. filtrationthe resulting solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-823888e42bcc4e1a9bffb8cb2a25fc5d
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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