Aluminium lithium hydride → HCID 10385470, compound

HRID 1768476Notes

Reaction equation

HRID 1768476 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][CH2:26][C:27](OC)=[O:28])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:17])[CH3:18])=[O:15])[C:11]([CH2:25][CH2:26][CH2:27][OH:28])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23614744HCID 23614744, compound

Product 1

HCID 10385470HCID 10385470, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.5 g (5.9 mmol) of ester 19-1 in THF at 0° C. was added 235 mg (6.2 mmol) of lithium aluminum hydride. After stirring for 30 min, the reaction was quenched with saturated NH4Cl, partitioned between EtOAc and 10% KHSO4, the organic phase was washed with water, saturated NaHCO3, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 19-2 as a white solid. Data for 19-2: HRMS (ES) calc'd M+H for C22H24F2N2O2: 387.1879. Found: 387.1877.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. custompartitioned between EtOAc and 10% KHSO4
  3. washthe organic phase was washed with water, saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-d3e43589116a457a8e354770dc6025c1
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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