Methyl iodide → HCID 13392998, compound

HRID 65079Notes

Reaction equation

HRID 65079 reaction equation
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][NH:5]1.[C:17](=[S:19])=[S:18].[CH2:20](N(CC)CC)C.CI>CO>[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH2:6][N:5]1[C:17]([S:19][CH3:20])=[S:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 13863924HCID 13863924, compound

Product 1

HCID 13392998HCID 13392998, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3R)-3-(2-Hydroxyethyl)-1,2,3,4-tetrahydro-β-carboline (94 mg) is dissolved in 80% methanol (2.4 ml), and thereto are added CS2 (0.026 ml) and triethylamine (0.061 ml). The mixture is stirred at room temperature for 30 minutes, and thereto is added dropwise methyl iodide (0.027 ml), and the mixture is stirred at room temperature for 4 hours. The reaction mixture is distilled to remove the solvent. The residue is dissolved in ethyl acetate. The solution is washed with water, dried over sodium sulfate and then distilled to remove the solvent. The residue is purified by thin layer chromatography (solvent, ethyl acetate:n-hexane=2:3) to give the title compound (51 mg, 38.3%) as colorless needles, m.p. 166°-167° C., NMR (CDCl3, δ): 2.72 (s, 3H, CSSCH3); Mass m/e: 306 (M+), 258 (M+ --CH3SH); [α]D20 -178.0° (c=0.1, methanol).

Workup

  1. stirringthe mixture is stirred at room temperature for 4 hours
  2. distillationThe reaction mixture is distilled
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washThe solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is purified by thin layer chromatography (solvent, ethyl acetate:n-hexane=2:3)

Sources & evidence

ORD record
ord-17aa8d10c79e46dbbaf3abc8f9a4a8bc
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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