Reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].C(O)C.[CH3:22]I.[C:24](=[S:26])=[S:25]>>[CH3:22][S:25][C:24]([N:2]1[C@@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:26]Participants
Procedure
To a mixture of (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (6.49 g), KOH (3.5 g) and 50% ethanol (110 ml) is added dropwise carbon disulfide (1.82 ml) under ice-cooling. The mixture is stirred at room temprature for one hour, and thereto is added dropwise methyl iodide (2.5 ml). The mixture is further stirred at room temperature for 4 hours. The reaction mixture is distilled to remove the solvent. The residue is dissolved in water. The solution is acidified with 10% HCl and extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1), and the product is crystallized from aqueous ethanol to give the title compound (5.5 g, 60%), m.p. 103°-106° C. (decomp.).
Workup
- temperaturecooling
- stirringThe mixture is further stirred at room temperature for 4 hours
- distillationThe reaction mixture is distilled
- customto remove the solvent
- dissolutionThe residue is dissolved in water
- extractionextracted with ethyl acetate
- washThe extract is washed with water
- customdried
- distillationdistilled
- customto remove the solvent
- customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=97:2:1)
- customthe product is crystallized from aqueous ethanol
Sources & evidence
- ORD record
- ord-5fde9dad733746b8b472e0332660f804
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628057
Linked notes
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