Benzyl (3S)-3-(4-morpholinylmethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate → (S)-4-((1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)morpholine

HRID 518920Notes

Reaction equation

HRID 518920 reaction equation
[N:1]1([CH2:7][C@@H:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][N:9]2C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[N:1]1([CH2:7][C@@H:8]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][NH:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 118482909Benzyl (3S)-3-(4-morpholinylmethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 28596890(S)-4-((1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)morpholine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4.9 g of the compound of Step B (13.4 mmol) in 67 mL of ethanol there is added 0.980 g of palladium dihydroxide (20% by weight) at ambient temperature. The reaction mixture is placed under 1.2 bars of hydrogen at ambient temperature for 4 hours. It is then passed through a Whatman filter and the palladium is then rinsed several times with ethanol. The filtrate is evaporated to dryness. The title product is obtained in the form of an oil.

Workup

  1. filtrationfilter
  2. washthe palladium is then rinsed several times with ethanol
  3. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-cb1bc9de6dfc4b0c92bef3f47c495221
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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