Aluminium lithium hydride → tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

HRID 1477903Notes

Reaction equation

HRID 1477903 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)([CH2:23][C:24]([F:27])([F:26])[F:25])[C:19](OC)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:18]([N:13]2[C:14]3[C:10](=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)([CH2:23][C:24]([F:26])([F:27])[F:25])[CH2:19][OH:20])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70563216methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)-4,4,4-trifluorobutanoate

Product 1

HCID 70561960tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step A (300 mg, 0.6 mmol) in THF (5 mL) was added LiAlH4 (38 mg, 0.96 mmol) at 0° C. The mixture was stirred at RT for 1 h and quenched with H2O (5 mL), extracted with ethyl acetate, and washed with brine (10 mL), dried over sodium sulfate, then filtered. After the solvent was removed, the residue was purified by silica gel chromatography (EA/PE=1:3) to afford the title compound. LC/MS m/z=470.1 [M+H]+.

Workup

  1. customquenched with H2O (5 mL)
  2. extractionextracted with ethyl acetate
  3. washwashed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customAfter the solvent was removed
  7. customthe residue was purified by silica gel chromatography (EA/PE=1:3)

Sources & evidence

ORD record
ord-a522840c8a764628bfd17e0659a74b01
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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