Tetrahydrofuran → 3-Hydroxymethyl-beta-carboline

HRID 1915006Notes

Reaction equation

HRID 1915006 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(OC)=[O:2].C1COCC1.[BH4-].[Na+]>O>[OH:2][CH2:1][C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 53533383-Hydroxymethyl-beta-carboline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-carbomethoxy-β-carboline or a derivative thereof (J in Scheme VII above) is dissolved in a polar solvent (e.g., THF), and a reducing agent (e.g., NaBH4) is added to the solution. The mixture is stirred for a few hours and cooled. An excess of water is then added, and the mixture is stirred for another few hours. The solvent is thereafter evaporated and the resulting residue is dissolved in water, washed several times with one or more non-polar solvents such as dichloromethane and ethyl acetate, and the combined organic extracts are then evaporated. The remaining residue is purified by column chromatography (e.g., on a silica gel with elution by a 9:1 mixture of ethylacetate and methanol), to give a 3-hydroxymethyl-β-carboline intermediate.

Workup

  1. temperaturecooled
  2. stirringthe mixture is stirred for another few hours
  3. customThe solvent is thereafter evaporated
  4. dissolutionthe resulting residue is dissolved in water
  5. washwashed several times with one or more non-polar solvents such as dichloromethane and ethyl acetate
  6. customthe combined organic extracts are then evaporated
  7. customThe remaining residue is purified by column chromatography (e.g.
  8. washon a silica gel with elution
  9. additionby a 9:1 mixture of ethylacetate and methanol),

Sources & evidence

ORD record
ord-2586272a565f4c7dbbf0cc94a4fed88c
Source dataset
uspto-grants-2013_12
Patent number
US08614319B2

Reaction notes

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