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

HRID 2272872Notes

Reaction equation

HRID 2272872 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 mass) at ambient temperature. The reaction mixture is placed under 1.2 bar of hydrogen at ambient temperature for 4 hours. It is subsequently passed over a Whatman filter, and then the palladium is 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 rinsed several times with ethanol
  3. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-b28f92a288b1455484884ee301d8b78a
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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