Potassium Carbonate → HCID 57855472, compound

HRID 1360646Notes

Reaction equation

HRID 1360646 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH2:26][CH3:27]>CN(C=O)C>[CH2:25]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 10562576Tert-butyl 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Product 1

HCID 57855472HCID 57855472, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of tert-butyl 7-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.2 g, 8 mmol) in anhydrous DMF (20 ml) was added potassium carbonate (2.43 g, 17 mmol) followed by propyl iodide (4.42 g, 26 mmol). The mixture was stirred at 75° C. for 16 hours, then evaporated under reduced pressure. The residue was taken up with EtOAc (50 ml) and washed with water and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to afford the titled compound as a solid (2.2 g, 88%) used in the next step without further purification. TLC—Chloroform/methanol (9/1): Rf=0.75. 1H-NMR (CDCl3, 400 MHz) δ 1.04 (3H, t), 1.50 (9H, s), 1.81 (2H, m), 2.76 (2H, m), 3.62 (2H, m), 3.91 (2H, m), 4.54 (2H, s), 6.65 (1H, s), 6.74 (1H, d), 7.04 (1H, d).

Workup

  1. customevaporated under reduced pressure
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-023e7ecfba9240b2aee687425f09e6a2
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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