Sodium Hydroxide → HCID 9797307, compound

HRID 428855Notes

Reaction equation

HRID 428855 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[NH:21][CH:22]=[CH:23][N:24]=3)[CH:15]=2)[CH3:13])[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>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[NH:24][CH:23]=[CH:22][N:21]=3)[CH:15]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22141244HCID 22141244, compound

Product 1

HCID 9797307HCID 9797307, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hexyl-6-[3-(1H-imidazol-2-yl)phenyl]-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 44, 190 mg, 0.56 mmol) in tetrahydrofluran (5 ml) at room temperature was added lithium aluminium hydride (1.1 ml, 1.12 nimol, 1.0 M in THF) dropwise over a few minutes. The mixture was heated under reflux for 1 hour 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:ammnonia solution (0.880) (90:10:1) to afford the title compound (140 mg, 74%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  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-6bf67f9587884f1791a91c778c251485
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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