Tetrabutylammonium Fluoride → HCID 10837375, compound

HRID 1077559Notes

Reaction equation

HRID 1077559 reaction equation
C[Si](CCOC([NH:10][C:11]1[N:12]=[CH:13][C:14]2[NH:15][C:16]3[C:21]([C:22]=2[C:23]=1[CH2:24][O:25][CH3:26])=[CH:20][C:19]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:18][CH:17]=3)=O)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:10][C:11]1[N:12]=[CH:13][C:14]2[NH:15][C:16]3[C:21]([C:22]=2[C:23]=1[CH2:24][O:25][CH3:26])=[CH:20][C:19]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[CH:18][CH:17]=3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86749703HCID 86749703, compound

Product 1

HCID 10837375HCID 10837375, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g of 3-trimethylsilylethoxycarbonylamino-6-benzyloxy-4-methoxymethyl-β-carboline in 40 ml of tetrahydrofuran is heated with 22 ml of tetrabutylammonium fluoride for 3 hours to 50° C. After distilling off the solvent it is taken up in ethyl acetate and washed once each with a saturated sodium-carbonate and saturated common salt solution. The organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride: ethanol=10:2 as eluant. After concentration by evaporation of the corresponding fractions and absorptive precipitation with cyclohexane/ethyl acetate, 1.32 g of 3-amino-6-benzyloxy-4-methoxymethyl-β-carboline is obtained.

Workup

  1. distillationAfter distilling off the solvent it
  2. washwashed once each with a saturated sodium-carbonate and saturated common salt solution
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with methylene chloride
  7. concentrationAfter concentration
  8. customby evaporation of the corresponding fractions and absorptive precipitation with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-00e1237daa6c476ea04f90d05121f8a9
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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