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

HRID 1249066

반응식

HRID 1249066 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-836bbc67d48f436686a50a33da215470
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04628057

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