D-Psicose → 8-Isoquinolinepropanol

HRID 1110480Notes

Reaction equation

HRID 1110480 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]#[C:12][CH2:13][OH:14])[CH:4]=[CH:3][N:2]=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.CO.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][CH2:13][OH:14])[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 2

HCID 441036D-PsicoseHCID 143474813-(8-Isoquinolinyl)-2-propyn-1-ol

Product 1

HCID 143474828-IsoquinolinepropanolYield 33.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 0.4 g of 3-(8-isoquinolinyl)-2-propyn-1-ol in a mixture of 10 mL of ethanol and 5 mL of methanol was hydrogenated over 0.06 g 10% Pd/C at room temperature and atmospheric pressure for 22 hours and then at 50 Psi for 20 hours. After the catalyst was removed by filtration and the filtrate was concentrated, the residual oil was purified by HPLC (methanol-chloroform; 1:19) and crystallized from ethyl acetate-hexane to yield 0.136 g of 8-isoquinolinepropanol, mp 66°-69° C.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residual oil was purified by HPLC (methanol-chloroform; 1:19)
  4. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8d26a6e44ba8477db379169b11f07a92
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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