Water → 3-Hydroxymethyl-beta-carboline

HRID 1915007Notes

Reaction equation

HRID 1915007 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].[BH4-].[Na+].O>C1COCC1>[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 962WaterHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 53533383-Hydroxymethyl-beta-carbolineYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 grams (15 mmol) of 3-carbomethoxy-β-carboline were suspended in 300 ml THF, 2.7 grams (75 mmol) sodium borohydride were added and the mixture was stirred at room temperature for 12 hours. The mixture was then cooled, 50 ml water was added and the resulting mixture was stirred overnight. The solvent was evaporated under reduced pressure and water (300 ml) was again added. The aqueous suspension was extracted with dichloromethane, followed by ethylacetate, the organic extracts were combined, and the solvent was evaporated under reduced pressure. The remaining residue was purified by column chromatography on silica gel, using and a 9:1 mixture of ethylacetate and methanol as eluent, to give 3-(hydroxymethyl)-β-carboline (2.5 grams, 81% yield).

Workup

  1. temperatureThe mixture was then cooled
  2. stirringthe resulting mixture was stirred overnight
  3. customThe solvent was evaporated under reduced pressure and water (300 ml)
  4. additionwas again added
  5. extractionThe aqueous suspension was extracted with dichloromethane
  6. customthe solvent was evaporated under reduced pressure
  7. customThe remaining residue was purified by column chromatography on silica gel
  8. additiona 9:1 mixture of ethylacetate and methanol as eluent

Sources & evidence

ORD record
ord-0238613b73c44eaa8b63b3536af361ee
Source dataset
uspto-grants-2013_12
Patent number
US08614319B2

Reaction notes

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