Ethyl Acetate → HCID 178444662, compound

HRID 1826349Notes

Reaction equation

HRID 1826349 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[NH:23][CH:22]=[N:21][N:20]=3)[CH:14]=2)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[NH3:7].[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([CH3:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[NH:23][CH:22]=[N:21][N:20]=3)[CH:14]=2)[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178444665HCID 178444665, compound

Product 2

HCID 222AmmoniaHCID 178444662HCID 178444662, compoundYield 180.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hexyl-6-methyl-6-[3-(4H-1,2,4-triazol-3-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 43, 220 mg, 0.65 mmol) in tetrahydrofuran (5 ml) at room temperature was added lithium aluminium hydride (1.3 ml, 1.30 mmol, 1.0M in THF) dropwise over a few minutes. The mixture was then heated under reflux for 2 hours and then cooled to 0° C. 2N sodium hydroxide (1.0 ml) was added cautiously followed by ethyl acetate (10 ml) and the mixture was stirred rapidly for 30 minutes, then filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by silica column chromatography eluting with ethyl acetate:methanol:ammonia solution (0.880) (80:20:1) to afford the title compound (190 mg, 90%) as a colourless oil.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 2 hours
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-9a7115cede354c30857f1f2ec8f988b3
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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