Aluminium lithium hydride → HCID 18706972, compound

HRID 1422094Notes

Reaction equation

HRID 1422094 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[C:13]2=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:15]([CH2:16][CH3:17])=[C:11]3[N:12]2[C:7](=[CH:8][CH:9]=[CH:10]3)[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH2:3][C:5]1[CH:6]=[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[N:12]2[C:13]=1[C:14]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)=[C:15]3[CH2:16][CH3:17])[CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53974404HCID 53974404, compound

Product 1

HCID 18706972HCID 18706972, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethyl-3-(4-hydroxyphenyl)pyrrolo[2,1,5-cd]indolizine-2-carboxylic acid dimethylamide (0.14 g, 0.37 mmol) was dissolved in 25 ml of dry tetrahydofurane under a nitrogen atmosphere. Lithium aluminium hydride (20 mg, 0.53 mmol) was added in portions and stirring was continued for 1/2 hours. The reaction mixture was quenched with 0.02 ml of water, 0.04 ml of a 2 M sodium hydroxide solution and then 0.04 ml of water again. The resulting precipitate was filtered off and washed with ethyl acetate. The solvent was removed and the crude product was purified by column chromatography over silica gel 60, using 10% of methanol in dichloromethane as the eluent. Fractions containing the product were collected and the solvent was evaporated to afford 63 mg (53%) of the title compound as a yellow solid. M.p. 176-178° C. MS(SP): m/z 318 (M+). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.35 (t, 3H); 2.27 (s, 6H); 3.10 (q, 2H); 3.94 (s, 2H); 6.98 (d, 2H); 7.25 (s, 1H); 7.57 (d, 2H); 7.72 (dd, 1H); 8.02 (d, 1H); 8.09 (d, 1H); 9.70 (s, 1H).

Workup

  1. customThe reaction mixture was quenched with 0.02 ml of water, 0.04 ml of a 2 M sodium hydroxide solution
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with ethyl acetate
  4. customThe solvent was removed
  5. customthe crude product was purified by column chromatography over silica gel 60
  6. additionFractions containing the product
  7. customwere collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b48c240ed02f4380bef95e9e0ba6f97b
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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