Aluminium lithium hydride → HCID 178519379, compound

HRID 591688Notes

Reaction equation

HRID 591688 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)(=O)C>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:16]1[O:15][CH2:14][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([CH2:3][OH:2])[CH:6]=2)[NH:10][N:9]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178497395HCID 178497395, compound

Product 1

HCID 178519379HCID 178519379, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

3-(Tetrahydro-pyran-2-yloxymethyl)-1H-indazole-5-carboxylic acid methyl ester (0.53 g crude, approximately 1.55 mmol) was taken in anhydrous THF (20 mL) and cooled to −10° C. A solution of lithium aluminium hydride (1.0 M solution in THF, 0.12 g, 3.10 mmol) was added drop-wise at −10° C. over a period of 15 minutes under nitrogen. Stirring continued at −10° C. for 1 hour and the reaction was then allowed to warm to room temperature and stirring continued at room temperature for 16 hours. The reaction mixture was carefully quenched with saturated aq. saturated ammonium chloride solution (100 mL). Then, reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was separated, washed with brine (50 mL) and dried over anhydrous Na2SO4. Solvent was evaporated to give [3-(tetrahydro-pyran-2-yloxymethyl)-1H-indazol-5-yl]-methanol as a yellow gummy material. Yield: 0.40 g (crude). This product was used in the next step without further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitcontinued at room temperature for 16 hours
  4. customThe reaction mixture was carefully quenched with saturated aq. saturated ammonium chloride solution (100 mL)
  5. customThen, reaction mixture
  6. customThe organic phase was separated
  7. washwashed with brine (50 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customSolvent was evaporated

Sources & evidence

ORD record
ord-9d0a45cad86b43ddb551697b45352656
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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