Tetrahydrofuran → HCID 22859584, compound

HRID 1441065Notes

Reaction equation

HRID 1441065 reaction equation
COC([C:5]1[C:6]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:20][C@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])=[N:7][CH:8]=[CH:9][CH:10]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:33]1CCC[CH2:34]1>>[OH:33][CH2:34][C:8]1[N:7]=[C:6]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:20][C@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:26])[CH:5]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 53721255HCID 53721255, compound

Product 1

HCID 22859584HCID 22859584, compound

Procedure

A solution of 5-(3-MethoxycarbonyI-2-pyridyl)-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole (393 mg, 1.073 mmol) (see Example 62) in tetrahydrofuran (2.5 ml) was added dropwise, with stirring, to a flask containing a solution of lithium aluminium hydride in tetrahydrofuran (35.9 mg of LiAIH4 in 10.0 ml THF) under a nitrogen atmosphere. The reaction was stirred for 24 hours whereupon the reaction mixture was quenched with aqueous sodium carbonate and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.7), to afford, after combination and evaporation of the appropriate fractions, the title compound as a white foam (298 mg). Found: C,71.55; H,6.93; N,12.20. C20H22N3O.1/5CH2Cl2 requires: C,71.70; H,6.97; N,12.42%.

Workup

  1. stirringThe reaction was stirred for 24 hours whereupon the reaction mixture
  2. customwas quenched with aqueous sodium carbonate
  3. extractionthe aqueous phase extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with dichloromethane/methanol/ammonium hydroxide (90:10:0.7)
  8. customto afford
  9. customafter combination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-be5eda73adfc43658ed3b523d8c6385d
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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