Methyl iodide → Methyl (3RS)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

HRID 1249066

反応式

HRID 1249066 の反応式
[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][CH:3]([C:14]([O:16][CH3:17])=[O:15])[NH:2]1.C(N(CC)CC)C.[C:25](=[S:27])=[S:26].[CH3:28]I>CO>[CH3:28][S:26][C:25]([N:2]1[CH:3]([C:14]([O:16][CH3:17])=[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:27]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 1777282,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

生成物 1

HCID 13561978Methyl (3RS)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate収率 65.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (2.30 g) is dissolved in methanol (50 ml) and thereto are added triethylamine (1.21 g) and carbon disulfide (920 mg). The mixture is stirred at room temperature for 20 minutes and thereto is added dropwise methyl iodide (1.70 g). The mixture is stirred for 4 hours and distilled under reduced pressure to remove the solvent. The residue is dissolved in ethyl acetate, and the mixture is washed with water, dried and distilled to remove the solvent. The residue is recrystallized from ether-n-hexane to give the title compound (2.10 g, 65.6%) as colorless needles, m.p. 132°-134° C.

後処理

  1. stirringThe mixture is stirred for 4 hours
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe mixture is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from ether-n-hexane

出典と根拠

ORDレコード
ord-836bbc67d48f436686a50a33da215470
出典データセット
uspto-grants-1986_12
特許番号
US04628057

関連ノート

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