Methyl 5-(benzyloxy)-2-isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylate → Methyl 5-hydroxy-2-isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

HRID 1177367Notes

Reaction equation

HRID 1177367 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]2=[O:23])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][N:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]2=[O:23]

Participants

4

Reactant 1

HCID 59559848Methyl 5-(benzyloxy)-2-isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

Product 1

HCID 59560203Methyl 5-hydroxy-2-isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(benzyloxy)-2-isobutyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (1 g, 2.72 mmol) in MeOH (10 mL) was added catalyst amount of 10% Pd on C. This mixture was stirred under H2 balloon at room temperature for 3 hr. The solids were filtered through a bed of Celite. Removal of the solvent gave the product (750 mg, 98%) as light yellow solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.97 (d, 6 H) 1.98-2.16 (m, 1 H) 3.05 (t, J=6.59 Hz, 2 H) 3.38-3.50 (m, 2 H) 3.57 (t, J=6.69 Hz, 2H) 3.82-3.93 (m, 3 H) 7.50 (s, 1 H) 7.74 (d, J=1.51 Hz, 1 H) 8.30 (d, J=1.32 Hz, 1 H); MS (ESI, pos): 278.

Workup

  1. filtrationThe solids were filtered through a bed of Celite
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-cbb703ea55ad4c1bac5dd187e0c417d4
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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