Sodium Hydroxide → 9-benzyl-3-hydroxymethyl-beta-carboline

HRID 1619477Notes

Reaction equation

HRID 1619477 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[N:18][C:17]([C:21](OCC)=[O:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[N:18][C:17]([CH2:21][OH:22])=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 13383905HCID 13383905, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 116162359-benzyl-3-hydroxymethyl-beta-carbolineYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 33 (3.3 g, 10 mmol) was mixed with anhydrous THF (100 ml). The mixture was added dropwise to a mixed solution of LiAlH4 (1.2 g, 30 mmol) and anhydrous THF (100 ml). After that, the mixture was refluxed for 10 h. Then the mixture was cooled to room temperature. 10% NaOH (50 ml) was added into the mixture and then stirred for 20 minutes. The mixture was extracted with ethyl acetate, the organic phases were combined and washed with water and brine, dried over anhydrous sodium sulfate, filtered, evaporated and purified by silica gel column chromatography with ethyl acetate as the eluent. Upon recrystallization, white solids (1.5 g, 52%) were obtained, mp 120-122° C.

Workup

  1. temperatureAfter that, the mixture was refluxed for 10 h
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by silica gel column chromatography with ethyl acetate as the eluent
  8. customUpon recrystallization

Sources & evidence

ORD record
ord-d3c97257082441658888f4c48dd3b8d1
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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