2-Benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline → 1-(1-Methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 2383047Notes

Reaction equation

HRID 2383047 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:18]([O:21][CH3:22])([CH3:20])[CH3:19])C1C=CC=CC=1>CO.[Pd]>[CH3:22][O:21][C:18]([CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1)([CH3:20])[CH3:19]

Participants

4

Reactant 1

HCID 593964802-Benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 593965841-(1-Methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinolineYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% palladium-supported carbon (300 mg) was added to a solution of 2-benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline (1.17 g) in MeOH (12 mL). The reaction material was stirred under a hydrogen atmosphere at room temperature for 8 hours. The reaction liquid was filtered through celite and the filtrate was concentrated under reduced pressure to obtain 1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline (770 mg).

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b34ac9b7fa3d4d91b036c939e3317781
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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