Water → 3-Hydroxymethyl-beta-carboline

HRID 1619474Notes

Reaction equation

HRID 1619474 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14](OCC)=[O:15])[N:2]=1.[Li+].[BH4-].O>C1COCC1>[OH:15][CH2:14][C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 105078Ethyl Beta-Carboline-3-CarboxylateHCID 4148881Lithium borohydride

Product 1

HCID 53533383-Hydroxymethyl-beta-carbolineYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 10 (7.0 g, 31 mmol) was dissolved in anhydrous THF (900 ml) followed by the addition of LiBH4 (3.4 g, 155 mmol). The mixture was stirred at room temperature for 9 h and then cooled. Water (100 ml) was added into the mixture and stirred overnight. Then the solvent was removed in reduced pressure. With the addition of water (500 ml), extraction was conducted with dichloromethane (1 L) and then with ethyl acetate. The organic phases were combined, concentrated in vacuum and purified by silica gel column chromatography with ethyl acetate/methane (3:1) as the eluent to afford white solids (5.0 g, 82%), and mp 228-230° C. (reference[2]: 225-228° C.).

Workup

  1. temperaturecooled
  2. stirringstirred overnight
  3. customThen the solvent was removed in reduced pressure
  4. additionWith the addition of water (500 ml), extraction
  5. concentrationconcentrated in vacuum
  6. custompurified by silica gel column chromatography with ethyl acetate/methane (3:1) as the eluent

Sources & evidence

ORD record
ord-a35895c8b8fb40f39355bf5d808d7ee4
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

Loading…