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

HRID 515887Notes

Reaction equation

HRID 515887 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-eb6c8c72153b4c7ca491a4a30951f7d1
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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