6-(Benzyloxy)-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline → 2-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 1713080Notes

Reaction equation

HRID 1713080 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([CH:28]3[CH2:31][CH2:30][CH2:29]3)[CH2:24][CH2:23]1)=[O:21])[CH2:13][CH2:12]2)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH:28]1([N:25]2[CH2:24][CH2:23][N:22]([C:20](=[O:21])[CH2:19][N:14]3[CH2:13][CH2:12][C:11]4[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=4)[CH2:15]3)[CH2:27][CH2:26]2)[CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 1

HCID 574205646-(Benzyloxy)-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 574206962-[2-(4-Cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 6-(benzyloxy)-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline (2.5 g, 5.96 mmol) in EtOH (30 ml) is added 10% Pd(OH)2/C (0.5 g). The mixture is hydrogenated at 45 psi for 2 hr. The mixture is filtered through celite and washed with EtOH. The solvent is removed under reduced pressure to give the title compound. MS (+VE) m/z 330.2 (M+1).

Workup

  1. filtrationThe mixture is filtered through celite
  2. washwashed with EtOH
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5ba63960bac84c3b8f805ffac644fa42
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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