Aluminium lithium hydride → HCID 68555288, compound

HRID 2381913Notes

Reaction equation

HRID 2381913 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([N:11]=O)[CH2:6][C:5]2([CH3:14])[CH3:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH2:11])[CH2:6][C:5]2([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866393625-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole

Product 1

HCID 68555288HCID 68555288, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-fluoro-3,3-dimethyl-1-nitroso-2,3-dihydro-1H-indole (4.03 g, 20.75 mmol) in THF (70 mL) at 0° C. is added a solution of LiAlH4 (40 mL, 40 mmol) in THF dropwise. The mixture is allowed to warm to rt and stirred overnight. The mixture is quenched with a saturated aqueous solution of Rochelle's Salt. The resulting mixture is stirred until a slurry is obtained. The organic phase is separated, washed with 10% aqueous HCl, saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 25% EtOAc in heptane to afford 5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-ylamine (3.51 g, 94%) as an oil. MS: 181 (M+H). 1H NMR (300 MHz, CD3Cl)): δ 6.85-6.78 (m, 1H), 6.75-6.68 (m, 2H), 3.44 (br s, 2H), 3.14 (s, 2H), 1.28 (s, 6H).

Workup

  1. customThe mixture is quenched with a saturated aqueous solution of Rochelle's Salt
  2. stirringThe resulting mixture is stirred until a slurry
  3. customis obtained
  4. customThe organic phase is separated
  5. washwashed with 10% aqueous HCl, saturated aqueous NaHCO3, water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel chromatography
  10. washeluting with 25% EtOAc in heptane

Sources & evidence

ORD record
ord-e2c07496046844f2961cfad1386e7688
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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