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

HRID 1249070Notes

Reaction equation

HRID 1249070 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]([O:16][CH2:17][CH3:18])=[O:15])[NH:2]1.C(N(CC)CC)C.[C:26](=[S:28])=[S:27].[CH3:29]I>C(O)C>[CH3:29][S:27][C:26]([N:2]1[C@H:3]([C:14]([O:16][CH2:17][CH3:18])=[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:28]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 1079579ethyl (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 13561983Ethyl (3S)-2-[(methylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as described in Example 53, ethyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (2.50 g), triethylamine (1.34 g), carbon disulfide (0.82 ml), ethanol (60 ml) and methyl iodide (0.84 ml) are reacted and treated. The product is recrystallized from ethyl acetate-n-hexane to give the title compound (2.55 g, 68%) as colorless prisms, m.p. 138°-140° C.

Workup

  1. customare reacted
  2. additiontreated
  3. customThe product is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b0209ac9f2e9498da3e391f85d850859
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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