Aluminium lithium hydride → HCID 67336208, compound

HRID 1672162Notes

Reaction equation

HRID 1672162 reaction equation
C([O:3][C:4]([C:6]1([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)[CH2:9][CH2:8][CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([NH:10][C:6]3([CH2:4][OH:3])[CH2:9][CH2:8][CH2:7]3)=[CH:19][CH:18]=2)[CH:14]=[N:15]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67336209HCID 67336209, compound

Product 1

HCID 67336208HCID 67336208, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-(1H-indazol-5-ylamino)-cyclobutanecarboxylic acid ethyl ester (1.68 g, 6.49 mmol) in THF (37 mL) at 0° C. and under nitrogen was added LiAlH4 (13.0 mL of a 1.0 M solution in THF, 13.0 mmol) dropwise over 2 minutes then the reaction mixture was warmed to ambient temperature. After 2 hours the reaction mixture was quenched by the addition of sodium sulfate decahydrate (2 g). The reaction mixture was filtered and the filter cake washed with EtOAc. The combined filtrates were concentrated in vacuo to a yellow solid. Purification by chromatography (silica, 4 to 20% of a 9:1 MeOH:NH4OH solution in DCM) gave [1-(1H-indazol-5-ylamino)-cyclobutyl]-methanol (0.827 g, 3.81 mmol, 59%) as a white powder.

Workup

  1. customAfter 2 hours the reaction mixture was quenched by the addition of sodium sulfate decahydrate (2 g)
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake washed with EtOAc
  4. concentrationThe combined filtrates were concentrated in vacuo to a yellow solid
  5. customPurification by chromatography (silica, 4 to 20% of a 9:1 MeOH:NH4OH solution in DCM)

Sources & evidence

ORD record
ord-227e1a3cc32f4c8bb3be19b897fca8f2
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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