4-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester → 4-Hydroxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester

HRID 523839Notes

Reaction equation

HRID 523839 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:11]2[C:16]([C:17]=1[O:18]CC1C=CC=CC=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]>[Pd].CCOC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:26][CH:27]([CH3:28])[CH3:29])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 667132624-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667127764-Hydroxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl esterYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-Benzyloxy-1-isobutyl-isoquinoline-3-carboxylic acid butyl ester (125 mg, 0.32 mmol), Pd/C (50 mg, Aldrich, 10 wt % Pd) and EtOAc (15 ml) were stirred at ambient pressure and temperature under an H2 atmosphere for 24 h. The mixture was then filtered through a pad of celite. Concentration of the filtrate in vacuo yielded the title compound as a yellowish oil (87 mg); MS-(+)-ion M+1=302.2.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite

Sources & evidence

ORD record
ord-d1eaa1497b194db3868f29593aedcb08
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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