Aluminium lithium hydride → HCID 69216097, compound

HRID 272761Notes

Reaction equation

HRID 272761 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH2:17][C:18](OC)=[O:19])[CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[CH:22]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH2:17][CH2:18][OH:19])[CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 91002123HCID 91002123, compound

Product 1

HCID 69216097HCID 69216097, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of Example 695D (6.32 g, 20 mmol) in 100 mL of THF was treated with 1.0 M LiAlH4 in THF (35 mL, 35 mmol) at 0° C. The reaction mixture was stirred for additional 30 minutes, quenched with MeOH, and concentrated under vacuum. The residue was partitioned between ethyl acetate and pH=3 water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:9 hexanes/ethyl acetate to provide 5.18 g (90%) of the desired product. MS (DCI) m/e 289 and 291 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.83 (s, 1H), 7.96 (s, 1H), 7.67 (d, J=8.5 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 6.91 (dd, J=8.5, 2.0 Hz, 1H), 6.81-6.84 (m, 3H), 4.59 (t, J=6.0 Hz, 1H), 3.51-3.53 (m, 2H), 2.58 (t, J=6.9 Hz, 2H).

Workup

  1. customquenched with MeOH
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between ethyl acetate and pH=3 water
  4. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel with 1:9 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-34fb8cb1ba604421ab800309793e16c0
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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