8-Phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril → 8-Hydroxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril

HRID 1090707Notes

Reaction equation

HRID 1090707 reaction equation
C1(C[O:8][C:9]2[CH:10]=[CH:11][C:12]([O:20][CH2:21][CH:22]([OH:38])[CH2:23][N:24]3[CH2:29][CH2:28][CH:27]([NH:30][C:31]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:32])[CH2:26][CH2:25]3)=[C:13]3[C:18]=2[NH:17][C:16](=[O:19])[CH2:15][CH2:14]3)C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:21][CH:22]([OH:38])[CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH:30][C:31]([O:33][CH2:34][CH:35]([CH3:36])[CH3:37])=[O:32])[CH2:26][CH2:25]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2

Participants

4

Reactant 1

HCID 199137998-Phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril2×

Product 1

HCID 156770648-Hydroxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8-Phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril, the compound from Step A above (160 mg), was dissolved in ethanol (15 mL). Palladium (10% on carbon) was added, and the mixture was stirred under hydrogen at room temperature for 48 hours. The catalyst was removed by filtration, and the solvent evaporated to give 100 mg of crude product which was recrystallized from aqueous ethanol, yielding the title compound, 8-hydroxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril, m.p. 199°-200° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. customto give 100 mg of crude product which
  4. customwas recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-ae0583f5f34240afbd7814e652420786
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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