3-Methoxypropyne → 5-(2-Chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-beta-carboline

HRID 1720333Notes

Reaction equation

HRID 1720333 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8]([CH2:21][O:22][CH3:23])=[C:9]([CH:18]=[N:19][OH:20])[N:10]=[CH:11][C:12]=1[NH:13]2.Cl[O-].[Na+].[CH3:31][O:32][CH2:33][C:34]#[CH:35]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8]([CH2:21][O:22][CH3:23])=[C:9]([C:18]3[CH:35]=[C:34]([CH2:33][O:32][CH3:31])[O:20][N:19]=3)[N:10]=[CH:11][C:12]=1[NH:13]2

Participants

6

Reactant 3

HCID 693933-MethoxypropyneHCID 23665760Sodium HypochloriteHCID 1363755795-(2-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde-oxime

Product 1

HCID 224177485-(2-Chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-beta-carbolineYield 8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.06 g (0.0028 mol) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carbaldehyde-oxime in 25 ml tetrahydrofuran is mixed with 10 ml of sodium hypochlorite solution at 35° C. under argon. After 20 minutes no more initial material can be detected by thin-layer chromatography. 0.32 ml (0.004 mol) of methylpropargylether is instilled at room temperature and it is stirred for 3 more hours. After being left standing overnight it is diluted with ethyl acetate, washed neutral with water, dried and concentrated by evaporation. The residue is chromatographically separated on silica gel with a mixture of 2 parts tetrahydrofuran and one part of toluene. First a fraction is isolated, which after recrystallization from a dichloromethane/cyclohexane mixture yields 0.1 g (8% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-3-(5-methoxymethylisoxazol-3-yl)-β-carboline, melting point 178°-180° C.

Workup

  1. customis instilled at room temperature
  2. waitAfter being left
  3. waitstanding overnight
  4. washwashed neutral with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographically separated on silica gel with a mixture of 2 parts tetrahydrofuran and one part of toluene
  8. customFirst a fraction is isolated
  9. customwhich after recrystallization from a dichloromethane/cyclohexane mixture

Sources & evidence

ORD record
ord-704529b46ea04a6eba0851af65bbf25e
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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