Aluminium lithium hydride → HCID 11132586, compound

HRID 440433Notes

Reaction equation

HRID 440433 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[F:30])[N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:30][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][C:24]=1[N:6]([N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8]1)[CH2:5][CH2:4][OH:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22407301HCID 22407301, compound

Product 1

HCID 11132586HCID 11132586, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-fluoro-4-pyridinyl)-N-(5-benzyloxy-1H-indol-1-yl)glycine ethyl ester (18.7 g) in 100 ml of tetrahydrofuran cooled to ice bath temperature, was added lithium aluminum hydride (89.16 ml) dropwise to the cool solution. The solution was stirred for 0.5 hour, then quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, MgSO4). After filtering, the solvent was evaporated to yield a solid (12.5 g) which was eluted with 50% ethyl acetate/dichloromethane on a silica gel column via HPLC. The desired fractions were evaporated to yield 9.65 g of a solid, m.p. 130°-132° C.

Workup

  1. customquenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried (sat. NaCl, MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d22381ae15884f9d80dc89630a05d0d5
Source dataset
uspto-grants-1996_05
Patent number
US05519131

Reaction notes

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