HCID 20814965, compound → HCID 22350074, compound

HRID 896687Notes

Reaction equation

HRID 896687 reaction equation
C([O:3][C:4](=O)[CH:5]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:23]([C:15]1[CH:16]=[C:17]2[C:22](=[C:13]([C:9]3[CH:8]=[C:7]([CH2:6][CH:5]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=4)[CH2:4][OH:3])[CH:12]=[CH:11][CH:10]=3)[CH:14]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 20814965HCID 20814965, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22350074HCID 22350074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of Example 66 (15 mg, 0.035 mmol) in THF (mL) at 0° C. was added LiAlH4 (1M, THF, 0.35 mL, 0.35 mmol) dropwise. The resulting reaction mixture was stirred 1 h at 0° C., 1 h at 21° C., and then quenched with water and neutralized using 1N HCl. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with ethanol/ethyl acetate, 1:9) provided the title compound.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with water
  3. washThe organic extracts were washed (H2O, brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby flash chromatography (eluting with ethanol/ethyl acetate, 1:9)

Sources & evidence

ORD record
ord-35632114221f4c5bbb8b5381365ffa55
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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