Aluminium lithium hydride → HCID 90460282, compound

HRID 1846257Notes

Reaction equation

HRID 1846257 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]2[C:23]([C:34](OCC)=[O:35])=[N:24][N:25]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[C:26]=2[CH3:27])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:22]2[C:23]([CH2:34][OH:35])=[N:24][N:25]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[C:26]=2[CH3:27])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90461300HCID 90461300, compound

Product 1

HCID 90460282HCID 90460282, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a mixture of LiAlH4 (60 mg, 1.58 mmol, 4.01 equiv) in anhydrous tetrahydrofuran (15 mL) maintained under nitrogen at −40° C. was added dropwise a solution of (R/S) ethyl 4-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate (180 mg, 0.39 mmol, 1.00 equiv) in tetrahydrofuran (5 mL). The reaction was stirred at −40° C. for 30 min then at 25° C. for 1 h. The reaction was quenched with 0.1 mL of saturated NH4Cl solution. The solid material was removed by filtration. The filtrate was extracted with 3×10 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 30-100% of ethyl acetate in petroleum ether to afford 70 mg (43%) of (R/S) (4-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)methanol as a colorless oil. LCMS (method A, ESI): RT=1.49 min, m/z=415.0 [M+H]+.

Workup

  1. waitat 25° C. for 1 h
  2. customThe reaction was quenched with 0.1 mL of saturated NH4Cl solution
  3. customThe solid material was removed by filtration
  4. extractionThe filtrate was extracted with 3×10 mL of ethyl acetate
  5. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column
  8. washeluted with 30-100% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-6b1452f3f7c5466b98d6e5b0fb522ad5
Source dataset
uspto-grants-2015_02
Patent number
US08952026B2

Reaction notes

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