Potassium Hydroxide → 6-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 352860Notes

Reaction equation

HRID 352860 reaction equation
C(O[C:4]([CH:6]1[NH:11][CH2:10][C:9]2[S:12][CH:13]=[N:14][C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[K+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH3:4][CH:6]1[NH:11][CH2:10][C:9]2[S:12][CH:13]=[N:14][C:8]=2[CH2:7]1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 225635076-Ethoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Product 1

HCID 227111356-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In anhydrous tetrahydrofuran (500 ml), 6-ethoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (WO94/21599) (21.0 g) was dissolved, followed by the addition of a solution of lithium aluminum hydride in tetrahydrofuran (a 1.0M solution, 200 ml) under ice cooling. The resulting mixture was stirred at room temperature for 2 hours. Water (7 ml) was then added slowly to the reaction mixture. After the termination of the reaction, a 1N aqueous potassium hydroxide solution (7 ml) and anhydrous magnesium sulfate were successively added. After removal of the insoluble matter by filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was purified by distillation under reduced pressure (1.5 mmHg, boiling point: 82 to 85° C.), whereby the title compound (6.10 g, 40%) was obtained as a colorless oil.

Workup

  1. customAfter the termination of the reaction
  2. customAfter removal of the insoluble matter
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. distillationwas purified by distillation under reduced pressure (1.5 mmHg, boiling point: 82 to 85° C.), whereby the title compound (6.10 g, 40%)
  7. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-f9288c7689034a35970dfafdf722ea3d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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