Colchicine → 3-Demethylcolchicine

HRID 2308994Notes

Reaction equation

HRID 2308994 reaction equation
[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:12]([O:24][CH3:25])=[C:11]([O:26][CH3:27])[C:10]([O:28]C)=[CH:9][C:8]=2[CH2:7][CH2:6]1)=[O:3]>CO>[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([OH:28])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3]

Participants

3

Reactant 1

HCID 6167Colchicine

Product 1

HCID 2996643-DemethylcolchicineYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the same procedure as for colchicine, after evaporating the solvents 10 ml of a 10% methanolic K2CO3 solution was added and the mixture stirred for 1 h. The MeOH was evaporated and cold 2N HCl was added until pH 6-7. Extraction with CHCl3, washing with brine, drying and evaporating gave a brown residue which was purified by flash chromatography (CHCl3 /MeOH 100:7) and crystallized from CHCl3 : 2 as a light yellow solid, (51% yield), mp 246°-248° C., [α]D25 0° (c 0.12, MeOH).

Workup

  1. customafter evaporating the solvents 10 ml of a 10% methanolic K2CO3 solution
  2. additionwas added
  3. customThe MeOH was evaporated
  4. additioncold 2N HCl was added until pH 6-7
  5. extractionExtraction with CHCl3
  6. washwashing with brine
  7. customdrying
  8. customevaporating
  9. customgave a brown residue which
  10. customwas purified by flash chromatography (CHCl3 /MeOH 100:7)
  11. customcrystallized from CHCl3

Sources & evidence

ORD record
ord-f4ede3c63d7c4c49ba789e88c2cf46e5
Source dataset
uspto-grants-1987_09
Patent number
US04692463

Reaction notes

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