HCID 19389968, compound → HCID 19389970, compound

HRID 1757149Notes

Reaction equation

HRID 1757149 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1([C:20](O)=[O:21])[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1>CCOC(C)=O>[NH2:7][C:8]1([CH2:20][OH:21])[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 19389968HCID 19389968, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19389970HCID 19389970, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 172 mg (0.00452 mol) of lithium aluminum hydride in 6 mL of THY at 0° C. was added portion-wise 500 mg (0.00226 mol) of the product of Step B. The mixture was refluxed overnight. EtOAc was carefully added to quench excess hydride and 50% aqueous NaOH added. The mixture was extracted with EtOAc and the EtOAc extract washed with brine. It was dried (MgSO4) and concentrated to give an oil which solidified on standing to give 390 mg of a tan solid: mp 89°-95.6° C. 1H NMR (DMSO-d6) d 7.422 (d, 1H), 6.70 (d, 1H), 6.95 (s, 1H), 3.690 (s, 3H), 3.20-3.40 (m, 3H), 2.70 (t, 2H), 2.0-2.20 (m. 2H), 1.70 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customto quench excess hydride and 50% aqueous NaOH
  3. additionadded
  4. extractionThe mixture was extracted with EtOAc
  5. extractionthe EtOAc extract
  6. washwashed with brine
  7. dry with materialIt was dried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil which

Sources & evidence

ORD record
ord-2ab3d13ad6144816af7b7f231439f7df
Source dataset
uspto-grants-1995_08
Patent number
US05444079

Reaction notes

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