Aluminium lithium hydride → HCID 58303925, compound

HRID 1404117Notes

Reaction equation

HRID 1404117 reaction equation
[CH3:1][N:2]([CH3:26])[C:3](=O)[CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:22])[CH:10]=[C:11]([CH2:16][CH2:17][C:18](OC)=[O:19])[C:12]=2[O:14][CH3:15])[N:7]([CH2:23][CH3:24])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:22])[CH:10]=[C:11]([CH2:16][CH2:17][CH2:18][OH:19])[C:12]=2[O:14][CH3:15])[N:7]([CH2:23][CH3:24])[CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58303961HCID 58303961, compound

Product 1

HCID 58303925HCID 58303925, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27-2 (150 mg, 0.42 mmol) in anhydrous THF (20 mL) was added LiAlH4 (78 mg, 2.05 mmol) and the mixture was stirred at room temperature for two hours. Na2SO4.10H2O was added, the solid was filtered off and washed with ethylacetate (20 mL). The filtrate was concentrated in under vacuum. The resulting residue was purified by column chromatographyon (DCM:MeOH=50:1) to afford compound 27-3 (30 mg, 23%) as a white solid. 1H-NMR (400 MHz, MeOD-d6): δ (ppm) 7.02 (s, 1H), 6.65 (d, J=13.2 Hz, 1H), 4.16 (q, J=6.8 Hz, 2H), 3.72 (s, 3H), 3.51 (t, J=6.6 Hz, 2H), 3.22-3.17 (m, 2H), 3.10-3.03 (m, 2H), 2.74 (s, 6H), 2.72-2.64 (m, 2H), 1.79-1.72 (m, 2H), 1.30 (t, J=7.2 Hz, 3H). LRMS: calc 322.4 and found: 323.0 [MH]+.

Workup

  1. filtrationthe solid was filtered off
  2. washwashed with ethylacetate (20 mL)
  3. concentrationThe filtrate was concentrated in under vacuum
  4. customThe resulting residue was purified by column chromatographyon (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-58f2857dd1204467aa62a1ddbeb242d9
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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