Ethyl Acetate → (1,2,3,4-Tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-yl)methanol

HRID 1498896Notes

Reaction equation

HRID 1498896 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[N:12]2[C:13]3[CH:19]=[CH:18][C:17]([C:20](OCC)=[O:21])=[CH:16][C:14]=3[N:15]=[C:11]2[CH2:10][CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH2:7]1[N:12]2[C:13]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:14]=3[N:15]=[C:11]2[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12493647Ethyl 1,2,3,4-tetrahydropyrido[1,2-a]benzimidazole-7-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 56598510(1,2,3,4-Tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.97 g, 51.9 mmol) was suspended in tetrahydrofuran (30 ml); and under an ice cooling, a solution (20 ml) of ethyl 1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyridine-7-carboxylate (6.34 g, 26.0 mmol) prepared in the Step 3-1-3 in tetrahydrofuran was slowly added thereto. After the mixture was stirred under an ice cooling for one hour, a saturated sodium bicarbonate solution (5 ml) was slowly added to the mixture at the same temperature while paying attention to the generation of heat. Further, ethyl acetate was slowly added to the mixture. The mixture was allowed to cool to a room temperature and filtered. The filtrate was thoroughly washed with chloroform. The filtrate was concentrated and purified by silica gel column chromatography (chloroform:methanol=20:1 to 10:1) to give the title compound (4.20 g, 80%) as a white powder.

Workup

  1. additionwas slowly added
  2. temperatureof heat
  3. filtrationfiltered
  4. washThe filtrate was thoroughly washed with chloroform
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography (chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-033e2211808241ac89679e8e9ccb00c1
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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