Ethyl Acetate → HCID 68642063, compound

HRID 1498965Notes

Reaction equation

HRID 1498965 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]2[C:14]3[CH:20]=[CH:19][C:18]([C:21](OCC)=[O:22])=[CH:17][C:15]=3[N:16]=[C:10]2[CH2:9]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]2[C:14]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][C:15]=3[N:16]=[C:10]2[CH2:9]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 68642064HCID 68642064, compound

Product 1

HCID 68642063HCID 68642063, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

lithium aluminum hydride (0.21 g, 5.40 mmol) was suspended in tetrahydrofuran (15 ml), and under an ice cooling, a solution (5 ml) of ethyl 2-methyl-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate (0.70 g, 2.70 mmol) prepared in the Step 38-1-6 in tetrahydrofuran was slowly added dropwise to the suspension. After the mixture was stirred for 30 minutes under an ice cooling, and a saturated sodium bicarbonate solution was slowly added to the mixture under an ice cooling. Ethyl acetate was slowly added to the resulting mixture, and the precipitate was removed by filtration. The residue separated by filtration was carefully washed with chloroform. The washings and the filtrate were concentrated together. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1 to 5:1) to give the title compound (0.56 g, 96%) as a white powder.

Workup

  1. additionwas slowly added dropwise to the suspension
  2. customthe precipitate was removed by filtration
  3. customThe residue separated by filtration
  4. washwas carefully washed with chloroform
  5. concentrationThe washings and the filtrate were concentrated together
  6. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1 to 5:1)

Sources & evidence

ORD record
ord-5cda12a2bb7c4647b75167f3c4380366
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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