Ethyl Acetate → HCID 68642115, compound

HRID 1498968Notes

Reaction equation

HRID 1498968 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C:19]2[N:11]([C:12]3[C:17]([N:18]=2)=[CH:16][C:15]([C:20](OCC)=[O:21])=[CH:14][CH:13]=3)[CH2:10][CH2:9][S:8]1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH2:7]1[C:19]2[N:11]([C:12]3[C:17]([N:18]=2)=[CH:16][C:15]([CH2:20][OH:21])=[CH:14][CH:13]=3)[CH2:10][CH2:9][S:8]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 68642093HCID 68642093, compound

Product 1

HCID 68642115HCID 68642115, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (76 mg, 2.00 mmol) was suspended in tetrahydrofuran (20 ml), and under an ice cooling, a solution (10 ml) of ethyl 3,4-dihydro-1H-2-thia-4a,9-diazafluorene-7-carboxylate (260 mg, 1.00 mmol) prepared in the Step 40-1-3 in tetrahydrofuran was slowly added to the suspension. After the mixture was stirred under an ice cooling for 30 minutes, under an ice cooling, a saturated sodium bicarbonate solution was slowly added to the mixture, and then ethyl acetate was added thereto. The resulting mixture was filtered, and the residue was washed with a mixture solution of chloroform and methanol. The filtrate was concentrated and purified by silica gel column chromatography (chloroform:methanol=50:1) to give the title compound (150 mg, 68%) as a white powder.

Workup

  1. additionwas slowly added to the suspension
  2. filtrationThe resulting mixture was filtered
  3. washthe residue was washed with a mixture solution of chloroform and methanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-f6be0823a75d439e96d062bd55dd618e
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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