Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol → 2-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol

HRID 1378652Notes

Reaction equation

HRID 1378652 reaction equation
C([N:8]1[CH:17]([CH2:18][CH2:19][OH:20])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1>[Pd].CO>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH:17]([CH2:18][CH2:19][OH:20])[NH:8]1

Participants

4

Reactant 1

HCID 22911385Racemic 2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol

Product 1

HCID 128748552-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(+)-2-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-3-yl)-ethanol (610 mg, 2.3 mmol) was hydrogenated at 40 p.s.i.g. on a Parr Apparatus (305 mg of 10% palladium-on-carbon catalyst; methanol/concentrated hydrochloric acid solvent (15 ml and 0.25 ml, respectively) for 5 hours. The catalyst was filtered, and the filtrate was concentrated in vacuo to an oil, which was dissolved in dilute aqueous (pH 9) sodium carbonate/methylene chloride (50 ml of each). The aqueous phase was separated and extracted with two 10 ml portions of methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a viscous colorless oil (quantitative yield).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo to an oil, which
  3. dissolutionwas dissolved in dilute aqueous (pH 9) sodium carbonate/methylene chloride (50 ml of each)
  4. customThe aqueous phase was separated
  5. extractionextracted with two 10 ml portions of methylene chloride
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f0b90df6326f4ae2a20d60171b5c8e4c
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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